4-Nitrobenzaldehyde → HCID 10661075、化合物

反応式

[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[PH2:12]([O:14][CH2:15][CH3:16])=[O:13].C(N(CC)CC)C.C([O:27][CH2:28][CH3:29])(=O)C>>[OH:9][CH:8]([P:12](=[O:13])([O:27][CH2:28][CH3:29])[O:14][CH2:15][CH3:16])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1

参加物

反応物 4

HCID 5414-Nitrobenzaldehyde

HCID 8471Triethylamine

HCID 8857Ethyl Acetate

HCID 178476775HCID 178476775、化合物

生成物 1

HCID 10661075HCID 10661075、化合物

実験手順

To a mixture of 4-nitrobenzaldehyde (8.56 g) and ethyl hypophosphite (7.81 g) was gradually added triethylamine (1.5 mL). After stirring for 1 hr., the reaction mixture was diluted with ethyl acetate and washed successively with 1N hydrochloric acid and water. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, and diethyl α-hydroxy-4-nitrobenzylphosphonate was obtained as crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). Recrystallization from ethyl acetate-hexane gave yellow prism crystals (4.62 g, yield 28%). melting point: 94–95° C.