1-(2',4'-Difluoro(1,1'-biphenyl)-4-yl)ethan-1-one → 3-(2',4'-Difluoro-4-biphenylyl)-2-butenoic acid

반응식

C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].C(OP(C[C:28]([OH:30])=[O:29])(OCC1C=CC=CC=1)=O)C1C=CC=CC=1.C([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:41]=2[F:47])=[CH:36][CH:35]=1)(=O)C>C1COCC1>[F:47][C:41]1[CH:42]=[C:43]([F:46])[CH:44]=[CH:45][C:40]=1[C:37]1[CH:36]=[CH:35][C:34]([C:5]([CH3:6])=[CH:7][C:28]([OH:30])=[O:29])=[CH:39][CH:38]=1

참가 물질

실험 절차

A solution of 21.4 g. of lithium diisopropylamide in 200 ml. of THF is added to a stirred solution of 32 g. of α-dibenzylphosphonoacetic acid (carboxymethylphosphonic acid dibenzyl ester) in 300 ml. of THF at -80°. Then a solution of 23.2 g. of 4-acetyl-2',4'-difluorobiphenyl in 250 ml. of THF is asdded. The mixture is stirred for 12 hours more, during which it is allowed to come to room temperature. The product Z--C(CH3)(OLi)--CH[P=O (OCH2C6H5)2 ]COOLi (Z is 2',4'-difluoro-4-biphenylyl), which is formed, is hydrolyzed with dilute acetic acid/ice. The customary work up gives 3-(2',4'-difluoro-4-biphenylyl)-2-butenoic acid, m.p. 193°-195°.