Water → Tert.-butyl 2-chloro-3-cyclopentyl-2,3-epoxy-butanoate

HRID 328073

反応式

HRID 328073 の反応式
[CH:1]1([C:6]([CH3:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:10]([Cl:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].CCCCCC.O>O1CCCC1>[Cl:18][C:10]1([O:7][C:6]1([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:8])[C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12]

参加物

6

反応物 4

HCID 962WaterHCID 8058HexaneHCID 22326Cyclopentyl methyl ketoneHCID 30164831,1-Dimethylethyl dichloroacetate

生成物 1

HCID 21443888Tert.-butyl 2-chloro-3-cyclopentyl-2,3-epoxy-butanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-30 °C

実験手順

A mixture of 12.3 g of cyclopentylmethyl ketone and 18.5 g of tert.-butyl dichloroacetate was cooled to -30° C with stirring under an inert atmosphere and a solution of 12.2 g of potassium tert.-butylate in 60 ml of tetrahydrofuran was added thereto at the said temperature. After returning to room temperature, hexane and water were added and the organic phase was separated, washed with water and dried over magnesium sulfate. The solvents were evaporated off to leave an oily residue of tert.-butyl 2-chloro-3-cyclopentyl-2,3-epoxy-butanoate. 26.5 g of the latter product was added to a solution of 3 g of lithium carbonate and 20 g of lithium bromide in 100 ml of hexamethylphosphorotriamide and after stirring for 1 hour at room temperature, petroleum ether and water were added thereto. The organic phase was washed with water, dried over magnesium sulfate and filtered. The solvent was evaporated to obtain an oily residue which was tert.-butyl 3-cyclopentyl-2-oxo-3-butenoate which was used as is for the next step.

後処理

  1. customAfter returning to room temperature
  2. customthe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvents were evaporated off

出典と根拠

ORDレコード
ord-5efebaedd46c470e8f15e08ae676c09b
出典データセット
uspto-grants-1977_04
特許番号
US04016158

関連ノート

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