Ammonium Chloride → Ethyl alpha,alpha-dichloro-6,6-dimethyl-4-oxo-3-oxabicyclo[3.1.0]hexane-2-acetate

HRID 67041Notes

Reaction equation

[Cl:1][C:2]([Cl:18])([CH:8]1[CH:13](Cl)[C:12]([CH3:16])([CH3:15])[CH2:11][C:10](=[O:17])[O:9]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].CC(C)([O-])C.[K+].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]([Cl:18])([CH:8]1[O:9][C:10](=[O:17])[CH:11]2[CH:13]1[C:12]2([CH3:16])[CH3:15])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of ethyl α,α,3-trichloro-3,4,5,6-tetrahydro-4,4-dimethyl-6-oxo-2H-pyran-2-acetate (3.43 g, 10.8 mmol) in 20 ml of tetrahydrofuran was cooled to -20° C. Potassium tert-butoxide was added in small portions while the mixture was stirred and maintained at -20° C. over a period of two hours. A total of 1.4 g (12.5 mmol) was added. Aqueous ammonium chloride was added and the mixture was extracted with methylene chloride. Purification by column chromatography gave 1.82 g of ethyl α,α-dichloro-6,6-dimethyl-4-oxo-3-oxabicyclo[3.1.0]hexane-2-acetate (60% yield).

Workup

additionA total of 1.4 g (12.5 mmol) was added
extractionthe mixture was extracted with methylene chloride
customPurification by column chromatography

Sources & evidence

ORD record: ord-5287b55cc6a94833aa1c36fb2f49fc5a
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04344884

Reaction notes

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