Acetic Acid → methyl N-formyl-alpha-(3-methoxycarbonylcyclobutylidene)glycinate
Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([CH:7]1[CH2:10][C:9](=O)[CH2:8]1)=[O:6].[N+:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])#[C-:13].C(O)(=[O:21])C>O1CCCC1>[CH:13]([NH:12][C:14](=[C:9]1[CH2:10][CH:7]([C:5]([O:4][CH3:3])=[O:6])[CH2:8]1)[C:15]([O:17][CH3:18])=[O:16])=[O:21]Participants
Procedure
To a suspension of sodium hydride (0.27 g, 6.63 mmol, 60% oil dispersion) in dry tetrahydrofuran (10 ml), was added dropwise with vigorous stirring a solution of 3-methoxycarbonylcyclobutanone (0.707 g, 5.52 mmol) and methyl isocyanoacetate (0.6 g, 6.07 mmol) in dry tetrahydrofuran (20 ml) over 5 minutes. The reaction mixture was stirred at room temperature for 2 hours, cooled to 0° C. and 10% aqueous acetic acid (20 ml) added dropwise. The organic solvent was removed in vacuo and the resulting solution extracted with dichloromethane (3×20 ml). The combined extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated to give an oil. The crude product was purified by flash chromatography, eluting with ethyl acetate-hexane (1:1, 3:2), to give methyl N-formyl-α-(3-methoxycarbonylcyclobutylidene)glycinate as a colourless oil.
Workup
- additionwas added dropwise
- temperaturecooled to 0° C.
- customThe organic solvent was removed in vacuo
- extractionthe resulting solution extracted with dichloromethane (3×20 ml)
- washThe combined extracts were washed with water
- dry with materialdried over anhydrous magnesium sulphate
- customevaporated
- customto give an oil
- customThe crude product was purified by flash chromatography
- washeluting with ethyl acetate-hexane (1:1, 3:2)
Sources & evidence
- ORD record
- ord-f531453a5889437ca68c2691d4ac31c8
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06054448
Reaction notes
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