Reaction equation
ClC(OCC(C)C)=O.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](/[CH:15]=[CH:16]/[C:17](O)=[O:18])[CH:10]=1.CN1CCOCC1.[BH4-].[Na+]>COCCOC.O>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](/[CH:15]=[CH:16]/[CH2:17][OH:18])[CH:10]=1Participants
Procedure
Isobutyl chloroformate (4.4 ml) was added dropwise to a suspension of (E)-3-(3-pyridyl)acrylic acid (5.0 g) and N-methylmorpholine (4.05 ml) in 1,2-dimethoxyethane (50 ml) under −18° C. After being stirred at the same temperature for 0.5 hour, a solution of sodium borohydride (1.86 g) in water (10 ml) was added to the mixture all at once. The resulting mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate as eluent. The fractions containing the objective compound were collected and evaporated under reduced pressure to give (E)-3-(3-pyridyl)-2-propen-1-ol (1.0 g) as an oil.
Workup
- extractionextracted with ethyl acetate
- washThe extract was washed with brine
- dry with materialdried over magnesium sulfate
- customevaporated under reduced pressure
- customThe residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate as eluent
- additionThe fractions containing the objective compound
- customwere collected
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-9b31fc68bee54b4091abcb4588b77935
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06924278B2
Linked notes
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