m-Chloroperbenzoic acid → Methyl 9-(3,3-dimethyloxiran-2-YL)-7-methyl-3-oxonon-6-enoate

HRID 436870Notes

Reaction equation

ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]([CH2:24][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])=[CH:14][CH2:15][CH2:16][C:17](=[O:23])[CH2:18][C:19]([O:21][CH3:22])=[O:20].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:9]1[C:27]([CH3:29])([CH3:28])[CH:26]1[CH2:25][CH2:24][C:13]([CH3:12])=[CH:14][CH2:15][CH2:16][C:17](=[O:23])[CH2:18][C:19]([O:21][CH3:22])=[O:20]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of 5.1 g of m-chloroperbenzoic acid in 50 ml of methylene chloride was added dropwise at -40° C. under a nitrogen atmosphere to a solution of 6 g of the product of Example 3 in 60 ml of methylene chloride and after stirring for 15 minutes at -20° C., the mixture was poured into a saturated aqueous sodium bicarbonate solution. The mixture was extracted with methylene chloride and the organic phase was washed with aqueous sodium bicarbonate solution and then with water, dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue was chromatographed over silica and was eluted with a 7-3 benzene-ethyl acetate mixture to obtain 3.1 g of methyl 10-epoxy-7,11-dimethyl-3-oxo-6-dodecenoate in the form of a colorless liquid with a refractive index nD25 = 1.4680.

Workup

extractionThe mixture was extracted with methylene chloride
washthe organic phase was washed with aqueous sodium bicarbonate solution
dry with materialwith water, dried over sodium sulfate
customevaporated to dryness under reduced pressure
customThe residue was chromatographed over silica
washwas eluted with a 7-3 benzene-ethyl acetate mixture

Sources & evidence

ORD record: ord-5c3cc8842b6646e785d53e673abfe5b8
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04028386

Reaction notes

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