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

HRID 2166562노트

반응식

HRID 2166562 반응식
[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]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 13053731ethyl alpha,alpha,3-trichloro-3,4,5,6-tetrahydro-4,4-dimethyl-6-oxo-2H-pyran-2-acetateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 13053732Ethyl alpha,alpha-dichloro-6,6-dimethyl-4-oxo-3-oxabicyclo[3.1.0]hexane-2-acetate수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-20 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-263fc2680f744562addcdd506b82dcd4
출처 데이터셋
uspto-grants-1983_06
특허 번호
US04387233

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