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One-pot synthesis of 2-(1-acyloxypentyl)benzoic acids

One-pot synthesis of 2-(1-acyloxypentyl)benzoic acids
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摘要 A one-pot synthesis of 2-（1-acyloxypcntyl） benzoic acids by trapping the carboxylatc/alkoxide dianion with acylating reagents following Grignard addition with n-BuMgBr to 2-formylbcnzoic acid was described. Compared with routine synthetic method, this novel procedure has the advantage of convenient operation and higher yields. A one-pot synthesis of 2-（1-acyloxypcntyl） benzoic acids by trapping the carboxylatc/alkoxide dianion with acylating reagents following Grignard addition with n-BuMgBr to 2-formylbcnzoic acid was described. Compared with routine synthetic method, this novel procedure has the advantage of convenient operation and higher yields.
作者 Zhen Li Min Yi Hua Zhang Yi Sheng Lai Si Xun Peng
机构地区 Center of Drug Discovery
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2008年第8期915-917,共3页 中国化学快报（英文版）
关键词 One-pot synthesis 3-n-Butyl-1（3H）-isobcnzofuranone 2-（1-Hydroxypcntyl）benzoic acid 2-（1-Acyloxypcntyl）-benzoic acids One-pot synthesis 3-n-Butyl-1（3H）-isobcnzofuranone 2-（1-Hydroxypcntyl）benzoic acid 2-（1-Acyloxypcntyl）-benzoic acids
分类号 O62 [理学—有机化学]
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参考文献5

  • 1[1](a) C.H.Yah,Y.P.Feng,J.T.Zhang,Acta Pharmacol.Sin.19 (2) (1998) 49; (b) X.Z.Zhu,X.Y.Li,J.Liu,Eur.J.Phatmacol.500 (2004) 221.
  • 2[2]Y.Zhang,L.Wang,L.Y.Zhang,X.L.Wang,Drug Dev.Res.63 (2004) 174.
  • 3[3]F.C.Engelhardt,Y.J.Shi,C.J.Cowden,et aL J.Org.Chem.71 (2) (2006) 480.
  • 4[4]General procedures for the synthesis of compounds 4a-4f:A suspension of n-BuMgBr (22 mmol) in Et2O (30 mL) was added porfionwise to a solution of 1(1.5 g,10 retool) in Et2O (50 mL) with stirring below -10 to 0 ℃,the mixture was then stirred at room temperature for 5 h.The acylating reagent (30 mmol) in Et2O was added dropwise to the mixture,which was stirred for 4h.After Et2O was removed,10% HC1 solution (40 mL) and THF (20 mL) were added,and the mixture was stirred for 1 h.THF was evaporated in vacuum,then the solution was extracted with Et2O,and the organic layer was collected,dried,concentrated.The residue was purified by column chromatography on silica gel ehited with petroleum ether/EtOAc/HAc (V:V:V= 10:1:0.2-4:1:0.2) to give the title compound as a white solid,which was crystallized from hexane.
  • 5[5]The data of 4a-4f-4a:1H NMR (300 MHz,CDCl3,δ ppm):0.90 (t,3H,J = 13.8 Hz),1.27-1.46 (m,4H),1.75-1.89 (m,2H),2.11 (s,3H),6.63 (q,1H,J = 12.6 Hz),7.32-7.40 (m,1H),7.55-7.59 (m,2H),8.06 (d,IH,J = 8.1 Hz),10.78 (br,1H); IR (KBr,v):1411,1579,1689,1735,2956 and 3447 cm-1; ESI-MS:m/z 523[2M+Na+]; Anal.Caled.for C14H18O4:C 67.18,H 7.25; Found:C 67.02,H 7.28; 4b:1H NMR (300 MHz,CDCl3,δ ppm):0.91 (t,3H,J = 13.8 Hz),1.32-1.41 (m,4H),1.86-1.91 (m,2H),4.11 (s,2H),6.78(q,1H,J = 12.6 Hz),7.36-7.42 (m,1H),7.56-7.62 (m,2H),8.08 (d,1H,J = 8.1 Hz),10.89 (br,1H); JR (KBr,v):1412,1691,1734,2958 and 3450 cm-1; ESI-MS:m/z 283[35ClM-H+],285[37ClM-H+]; Anal.Calcd.for C14H17ClO4:C 59.05,H 6.02; Found:C 59.21,H 6.01; 4c:1H NMR (300 MHz,CDCl3,δ ppm):0.90 (t,3H,J= 14.1 Hz),1.26-1.47 (m,4H),1.85-1.90(m,2H),2.78 (t,2H,J = 10.5 Hz),3.72 (t,2H,J = 10.1 Hz),6.65 (q,1H,J = 12.4 Hz),7.31-7.35 (m,1H),7.53-7.59 (m,2H),8.05 (d,1H,J = 8.1 Hz),10.78 (br,1H); IR (KBr,v):1415,1576,1686,1731,2959 and 3445 cm-1; ESI-MS:m/z 341[79BrM-H+],343[81BrM-H+]; Anal.Calcd.for C15H19BrO4:C 52.49,H 5.58; Found:C 52.61,H 5.49; 4d:1H NMR (300 MHz,CDCl3,δ ppm):0.92 (t,3H,J = 14.4 Hz),1.39-1.54 (m,4H),2.05 (q,2H,J = 21.6 Hz),6.99 (t,IH,J = 12.5 Hz),7.38-7.41 (t,1H,J = 14.7 Hz),7.55-7.62 (m,2H),8.1 (d,1H,J = 8.1 Hz),8.25-8.31 (m,4H),10.92 (br,1H); IR (KBr,v):1415,1689,1736,2959 and 3451 cm-1; ESI-MS:m/z 712[2M-H+]; Anal.Calcd.for C19H19NO6:C 63.86,H 5.36,N 3.92; Found:C 63.65,H 5.42,N 3.84; 4e:1H NMR (300 MHz,CDCl3,δ ppm):0.91 (t,3H,J= 13.9 Hz),1.29-1.46 (m,4H),1.96-2.04 (m,2H),6.73 (q,1H,J= 12.8 Hz),7.33-7.53 (m,6H),7.95-7.99 (m,2H),8.05 (d,1H,J= 8.1 Hz),10.81 (br,1H); IR (KBr,v):1416,1684,1735,2955 and 3448 cm-1; ESI-MS:m/z 623[2M-H+]; Anal.Calcd.for C19H20O4:C 73.06,H 6.45; Found:C 72.87,H 6.51; 4f:1H NMR (300 MHz,CDCl3,δ ppm):0.89 (t,3H,J = 13.8 Hz),1.23-1.41 (m,4H),1.94-2.03 (m,2H),3.73 (s,3H),6.61 (q,1H,J = 12.4 Hz),6.91-6.94 (m,2H),7.31-7.38 (m,1H),7.53-7.58 (m,2H),7.84-7.88 (m,2H),8.06 (d,1H,J = 8.1 Hz),10.58 (br,1H); IR (KBr,v):1415,1685,1733,2951 and 3443 cm-1; ESI-MS:m/z 683[2M-H+]; Anal.Caled.for C20H22O5:C 70.16,H 6.48; Found:C 70.31,H 6.42.
Chinese Chemical Letters
2008年 第8期

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