Ethyl diazoacetate → Cyclobutoxyacetic Acid Ethyl Ester

HRID 18829Notes

Reaction equation

HRID 18829 reaction equation
[CH:1]1([OH:5])[CH2:4][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][CH:1]1[CH2:4][CH2:3][CH2:2]1)[CH3:13]

Participants

6

Reactant 2

HCID 12192Ethyl diazoacetateHCID 76218Cyclobutanol

Product 1

HCID 62115785Cyclobutoxyacetic Acid Ethyl EsterYield 70.2%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of cyclobutanol (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 30 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 140° C. to give 1.00 g of the product 469. 1H NMR (CDCl3) δ 4.21 (q, 2H), 4.03 (m, 1H), 3.98 (s, 2H), 2.28-2.15 (m, 2H), 2.08-1.95 (m, 2H), 1.7 (q, 1H), 1.50 (m, 1H), 1.28 (t, 3H)

Workup

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 140° C.

Sources & evidence

ORD record
ord-bff3feea9180468ea0515afe85495ec3
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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