Methyl 3-phenylpropionate → 5-chloro-2-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyloxy]benzenepropanoic acid

반응식

COC(=O)CCC1C=CC=CC=1.[OH:13][C:14]1[CH:24]=[CH:23][C:17]2[C:18](=[O:22])[CH2:19][CH2:20][O:21][C:16]=2[C:15]=1[CH2:25][CH2:26][CH3:27].C[O:29][C:30](=[O:47])[CH2:31][CH2:32][C:33]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=1[O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]Br>>[Cl:39][C:37]1[CH:36]=[CH:35][C:34]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][O:13][C:14]2[CH:24]=[CH:23][C:17]3[C:18](=[O:22])[CH2:19][CH2:20][O:21][C:16]=3[C:15]=2[CH2:25][CH2:26][CH3:27])=[C:33]([CH2:32][CH2:31][C:30]([OH:47])=[O:29])[CH:38]=1

참가 물질

반응물 3

HCID 7643Methyl 3-phenylpropionate

HCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one

HCID 543914602-[(5-Bromopentyl)oxy]-5-chlorobenzenepropanoic acid methyl ester

생성물 1

HCID 152950005-chloro-2-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyloxy]benzenepropanoic acid수율 71%

실험 절차

Using the procedure of example 4, 5-chloro-2-[5-[3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyloxy]benzenepropanoic acid methyl ester, a pale-yellow oil, was prepared in quantitative yield starting from 0.62 g (3 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one and 1.21 g (3.33 mmol) of 2-[(5-bromopentyl)oxy]-5-chlorobenzenepropanoic acid methyl ester. Saponification using the procedure of example 4 afforded 1.01 g (71%) of 5-chloro-2-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyloxy]benzenepropanoic acid as a colorless solid, mp 101°-103° C.