Methyl butyrate → HCID 89526418, compound
Reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[CH2:2][CH2:3][CH3:4].[Li+].CC([N-]C(C)C)C.[CH3:16][C:17]([S:20]([N:22]=[C:23]1[CH2:26][O:25][CH2:24]1)=[O:21])([CH3:19])[CH3:18]>C1COCC1>[C:17]([S:20]([NH:22][C:23]1([CH:2]([CH2:3][CH3:4])[C:1]([O:6][CH3:7])=[O:5])[CH2:26][O:25][CH2:24]1)=[O:21])([CH3:16])([CH3:18])[CH3:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Methyl butyrate (5.67 g, 55.5 mmol) was dissolved in anhydrous THF (100 mL) and cooled to −78° C. under nitrogen. LDA (2M solution in THF 27.1 mL, 54.2 mmol) was added drop-wise. After 1 hour at −78° C., a solution of 2-methyl-N-oxetan-3-ylidene-propane-2-sulfinamide (Preparation 39, 2.43 g, 13.88 mmol) in anhydrous THF (10 mL) was added. The reaction was gradually warmed to room temperature and stirred for 18 hours. The reaction was quenched with a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the title compound as an oil (2.89 g, 75% yield).
Workup
- temperatureThe reaction was gradually warmed to room temperature
- customThe reaction was quenched with a saturated aqueous solution of ammonium chloride
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-eb5517f68f3541ff9df7b6af23c5f5d6
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079878B2
Reaction notes
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