Diketene → Cyclopropylmethyl 3-oxobutanoate

HRID 543554Notes

Reaction equation

HRID 543554 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[CH2:6]=[C:7]1[O:11][C:9](=[O:10])[CH2:8]1>[H-].[Na+]>[C:9]([O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)(=[O:10])[CH2:8][C:7]([CH3:6])=[O:11]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 75644Cyclopropanemethanol

Product 1

HCID 10012135Cyclopropylmethyl 3-oxobutanoateYield 93%

Reagents, catalysts & solvents 1

HCID 24758Sodium hydrideCatalyst

Procedure

0.1 g of sodium hydride (50%) was added to 25 g of cyclopropylmethanol and then 29 g of diketene was added dropwise thereto at a temperature of 50° to 60° C. with stirring. After completion of the addition, the mixture was heated at that temperature for 1 hour. The resulting oil was distilled under reduced pressure to obtain 50 g (93% yield) of cyclopropylmethyl acetoacetate as a colorless oil having a boiling point of 78° C. (4 mmHg).

Workup

  1. additionAfter completion of the addition
  2. temperaturethe mixture was heated at that temperature for 1 hour
  3. distillationThe resulting oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-08e554ac758b4a40843217f7f54f749f
Source dataset
uspto-grants-1984_05
Patent number
US04446325

Reaction notes

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