3-Methyl-2-butanone → Tert.butyl 2-chloro-2,3-epoxy-3-isopropyl-butanoate

HRID 1578919Notes

Reaction equation

HRID 1578919 reaction equation
[CH:1]([C:4]([CH3:6])=[O:5])([CH3:3])[CH3:2].Cl[CH:8]([Cl:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>O1CCCC1>[Cl:16][C:8]1([O:5][C:4]1([CH:1]([CH3:3])[CH3:2])[CH3:6])[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10]

Participants

4

Reactant 2

HCID 112513-Methyl-2-butanoneHCID 30164831,1-Dimethylethyl dichloroacetate

Product 1

HCID 21443884Tert.butyl 2-chloro-2,3-epoxy-3-isopropyl-butanoateYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 122 g of potassium tert.-butylate in 720 ml of tetrahydrofuran was added at -20°C with stirring under an inert atmosphere to a mixture of 95 g of methyl isopropyl ketone and 185 g of tert.butyl dichloroacetate and after returning the temperature to room temperature, the mixture was stirred for 2 hours. The mixture was poured into ice water and the mixture was stirred and the organic phase was separated. The organic phase was washed with aqueous sodium chloride solution, dried over magnesium sulfate, passed through vegetable charcoal and concentrated to dryness to obtain 230.4 g of tert.butyl 2-chloro-2,3-epoxy-3-isopropyl-butanoate.

Workup

  1. customto room temperature
  2. stirringthe mixture was stirred
  3. customthe organic phase was separated
  4. washThe organic phase was washed with aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6645c7a19f794d5cb248a61f7054dc52
Source dataset
uspto-grants-1976_02
Patent number
US03940354

Reaction notes

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