Ethyl diazoacetate → (1-Cyclopropyl-1-ethoxy)acetic Acid Ethyl Ester

HRID 2053621Notes

Reaction equation

HRID 2053621 reaction equation
[CH:1]1([CH:4]([OH:6])[CH3:5])[CH2:3][CH2:2]1.[N+](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][O:6][CH:4]([CH:1]1[CH2:3][CH2:2]1)[CH3:5])[CH3:14]

Participants

6

Reactant 2

HCID 12192Ethyl diazoacetateHCID 791041-Cyclopropylethanol

Product 1

HCID 68565879(1-Cyclopropyl-1-ethoxy)acetic Acid Ethyl EsterYield 71.6%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of cyclopropyl-1-ethanol (860 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 130° C. to give 1.11 g of the product 471. 1H NMR (CDCl3) δ 4.12 (s, 2H), 4.10 (q, 2H), 2.86 (m, 1H), 1.25-1.15 (m, 6H), 0.8-0.7 (m, 1H), 0.55-0.3 (m, 3H), 0.05-0.02 (m, 1H); MS: m/z 173 (M++i).

Workup

  1. filtrationfiltered through celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 130° C.

Sources & evidence

ORD record
ord-d2e4b053d5ed4636b685b25f7da1a08e
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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