Benzaldehyde → HCID 70377050, compound
Reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].CN(C)P(N(C)C)(N(C)C)=[O:15].[CH:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O1[CH2:35][CH2:34][CH2:33][CH2:32]1>>[C:8]1(/[CH:4]=[CH:3]\[CH2:2][CH2:1][CH2:32][CH2:33][CH2:34][CH2:35][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23]([OH:15])=[O:30])[CH:7]=[CH:6][CH:11]=[CH:10][CH:9]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
A mixture of the compound of Example 15(a) (1.4 g, 4.5 mmoles) and tetrahydrofuran (15 ml) under argon was cooled to -78° C. with a dry ice acetone bath. A 26M solution of n-butyllithium in hexane (3.55 ml, 9 mmoles) was added dropwise. The resulting red-orange solution was stirred at -78° C. for 30 minutes. Hexamethylphosphoramide (5.5 ml) was added in one portion followed by benzaldehyde (0.41 ml, 4 mmoles) in tetrahydrofuran (5 ml). The reaction mixture was stirred under argon for 30 minutes. The tetrahydrofuran was evaporated and the residue was dissolved in ether and washed with cold 3N hydrochloric acid. The combined organic phase was dried over magnesium sulfate, filtered and evaporated. The crude material was then chromatographed on silica gel eluted with 4% ethyl acetate in hexane plus 1% formic acid to yield the desired compound.
Workup
- stirringThe reaction mixture was stirred under argon for 30 minutes
- customThe tetrahydrofuran was evaporated
- dissolutionthe residue was dissolved in ether
- washwashed with cold 3N hydrochloric acid
- dry with materialThe combined organic phase was dried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe crude material was then chromatographed on silica gel
- washeluted with 4% ethyl acetate in hexane plus 1% formic acid
Sources & evidence
- ORD record
- ord-d53d2cc045ae418993be1514c0a43900
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04871771
Reaction notes
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