Benzene → 3-(2-Ethoxycarbonyl-vinyl)-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester

Reaktionsgleichung

[C:1]([O:5][C:6]([CH:8]1[CH:14](C=O)[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28]([CH:33]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:30][CH2:31][CH3:32])=[O:29].[CH:53]1C=CC=CC=1>>[C:1]([O:5][C:6]([CH:8]1[CH:14]([CH:53]=[CH:33][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Komponenten

Edukt 3

HCID 241Benzene

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

HCID 539203363-Formyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester

Produkt 1

HCID 537577263-(2-Ethoxycarbonyl-vinyl)-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester

Versuchsvorschrift

To a solution of 3-Formyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester (310 mg, 0.78 mmoL) in 8.1 mL benzene was added (Carboethoxymethylene) triphenylphosphorane (408 mg, 1.17 mmoL) at ambient temperature. An additional 310 mg was added after 24 hours, after which the reaction was allowed to proceed for 72 hours. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph (silica: 18% to 25% ethyl acetate in hexanes) to yield 3-(2-Ethoxycarbonyl-vinyl)-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid tert-butyl ester; MS: (M+H)+ =468, (M+NHY4)- =485.