Water → Isohexane ethyl acetate
Reaction equation
[CH2:1]([O:3][C:4]([CH:6]=P([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22]C=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])[CH3:2].[CH:26]([N:29]=[C:30]=[S:31])([CH3:28])[CH3:27].Br[CH:33]([CH3:40])[C:34](=O)[C:35]([O:37][CH3:38])=[O:36].O.[CH2:42]1COCC1>>[CH3:20][CH2:25][CH2:24][CH:23]([CH3:22])[CH3:26].[C:4]([O:3][CH2:1][CH3:2])(=[O:5])[CH3:6].[CH3:40][C:33]1[S:31][C:30]([NH:29][CH:26]([CH3:28])[CH3:27])=[C:6]([C:4]([O:3][CH3:1])=[O:5])[C:34]=1[C:35]([O:37][CH2:38][CH3:42])=[O:36]Participants
7
Conditions
- Temperature
- -78 °C
Procedure
Ethoxycarbonylmethylene triphenyl phosphorane (33.8 g) in dry THF (200 ml) was treated with isopropyl isothiocyanate (10.1 g) at 65° C. for 16 h under nitrogen. The mixture was cooled to −78° C. and methyl 3-bromo-2-oxo-butanoate (19.5 g) was added. The reaction was allowed to warm slowly to room temperature. After 24 h at room temperature more methyl 3-bromo-2-oxo-butanoate (2.8 g) was added and the mixture was warmed to 60° C. for 16 h. The cooled reaction was poured into water (1.5 L) and extracted into ether. Drying and evaporation gave an oil which was chromatographed (SiO2/10:1 isohexane-ethyl acetate then 5:1 isohexane-ethyl acetate) to afford the subtitle compound (23.5 g).
Workup
- temperatureto warm slowly to room temperature
- temperaturethe mixture was warmed to 60° C. for 16 h
- customThe cooled reaction
- extractionextracted into ether
- customDrying
- customevaporation
- customgave an oil which
- customwas chromatographed (SiO2/10:1 isohexane-ethyl acetate
Sources & evidence
- ORD record
- ord-d915d49ef73b40cf80367b83fae5e037
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07361660B2
Reaction notes
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