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

HRID 67041ノート

反応式

HRID 67041 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5287b55cc6a94833aa1c36fb2f49fc5a
出典データセット
uspto-grants-1982_08
特許番号
US04344884

反応ノート

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