Ethyl diazoacetate → Ethyl 2-(benzyloxymethyl)cyclopropanecarboxylate

HRID 496051

Reaction equation

HRID 496051 reaction equation
[N+](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-].[CH2:9]([O:16][CH2:17][CH:18]=[CH2:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCOCC>[CH2:9]([O:16][CH2:17][CH:18]1[CH2:19][CH:3]1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetate2×HCID 84542Allyl benzyl ether

Product 1

HCID 22325150Ethyl 2-(benzyloxymethyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

31.2 g of ethyl diazoacetate are added to a solution of 0.3 mol of allyl benzyl ether in 150 ml of ether with the aid of a push-syringe. After stirring for 16 hours, 31.2 g of ethyl diazoacetate are added again. After 24 hours the mixture is filtered. The organic phase is washed with saturated NaHCO3 solution and then treated in customary manner. Chromatography over silica gel (dichloromethane) allows the expected product to be obtained.

Workup

  1. filtrationAfter 24 hours the mixture is filtered
  2. washThe organic phase is washed with saturated NaHCO3 solution
  3. additiontreated in customary manner
  4. customto be obtained

Sources & evidence

ORD record
ord-c809cba580fc45cd9cee4bfaa41681aa
Source dataset
uspto-grants-2005_09
Patent number
US06943184B2

Linked notes

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