Ethyl diazoacetate → Ethyl 2-(cyclopropylmethoxy)acetate

HRID 2053618

Reaction equation

HRID 2053618 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), 0.2t6-0.51 (m, 2H), 0.25-0.2 (m, 2H); 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-0c63c443ff8a4e19a9d0b0a75f46c3bb
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

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