4-trimethylsilylaniline → 12,12-Difluorododec-11-enoic acid N-(4-trimethylsilylphenyl)amide
Reaction equation
CO[C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[C:14]([F:16])[F:15].[CH3:18][Si:19]([CH3:28])([CH3:27])[C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[CH3:18][Si:19]([CH3:28])([CH3:27])[C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[C:14]([F:15])[F:16])=[CH:22][CH:21]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2.5 g of 12,12-difluorododec-11-enoic acid methyl ester are added at room temperature to 1.53 g of 4-trimethylsilylaniline in 25 ml of toluene. The mixture is stirred for 2 hours at 80° and then concentrated by evaporation in vacuo. The residue is taken up in toluene, the toluene phase is washed with water, dried over sodium sulfate and concentrated to dryness by evaporation. The residue is taken up in hexane:ethyl acetate (9:1) and filtered over silica gel. Evaporation of the filtrate yields the title compound (nD24 =1.5038; compound no. 1-2).