Ethyl diazoacetate → Ethyl 2-(cyclopropylmethoxy)acetate

HRID 18827

Reaction equation

HRID 18827 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[N+](=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)[CH3:13]

Participants

6

Reactant 2

HCID 12192Ethyl diazoacetateHCID 75644Cyclopropanemethanol

Product 1

HCID 43119684Ethyl 2-(cyclopropylmethoxy)acetateYield 85.7%

Reagents, catalysts & solvents 3

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

To a solution of cyclopropylmethanol (720 mg, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.0 mmol). The reaction mixture is stirred at rt for 5 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 1.22 g of the product 462. 1H NMR (CDCl3) δ 4.2 (q, 2H), 4.09 (s, 2H), 3.37 (d, 2H), 1.27 (t, 3H), 1.09 (m, 1H), 0.56-0.51 (m, 2H), 0.25-0.2 (m, 211); MS: m/z 191 (M+)

Workup

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 150° C.

Sources & evidence

ORD record
ord-43fbd85eb1b048678a5364b29514bed8
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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