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 17(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 2.6 M 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 3 N 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 3 N 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-5c26303341824d698c82af8b908010a2
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04730005
Reaction notes
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