Methanol → Methyl 4-(oxiran-2-yl)butanoate
Reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].ClC[CH:9]1[O:14][C:13](=O)[CH2:12][CH2:11][CH2:10]1.[CH3:16]O>>[O:14]1[CH2:9][CH:13]1[CH2:12][CH2:11][CH2:10][C:1]([O:2][CH3:16])=[O:4]Participants
Procedure
67.9 mg (0.492 mmol) of potassium carbonate were added to a mixture of 48.7 mg (0.328 mmol) of (-)-6-chloromethyltetrahydropyran-2-one obtained in Example 5 and 1 ml of methanol under water cooling, and the solution was then stirred for 30 minutes and further at room temperature for 5 hours. After distilling off with methanol, 10% hydrochloric acid was added to the resultant residue to neutralize the same, and it was then extracted with dichloromethane, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off to obtain 35.4 mg (yield 75%) of pure (-)-methyl 5,6-epoxyhexanoate [a compound of the formula (6')] as the residue. The values of physical properties of this product were good and comparable to those of literature [M. Suzuki et al., Chem. Pharm. Bull., 38, 2381 (1990)].
Workup
- distillationAfter distilling off with methanol, 10% hydrochloric acid
- additionwas added to the resultant residue
- extractionwas then extracted with dichloromethane
- dry with materialby drying over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-367f1b417dd0404cb64232e5c181ce1e
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05292891
Reaction notes
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