Cyclopentanol → Ethyl 2-(cyclopentyloxy)acetate

HRID 18821

Reaction equation

HRID 18821 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][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:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:14]

Participants

6

Reactant 2

HCID 7298CyclopentanolHCID 12192Ethyl diazoacetate

Product 1

HCID 43119653Ethyl 2-(cyclopentyloxy)acetateYield 67.1%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of cyclopentanol (0.91 mL, 9.5 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 overnight. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue vacuum distilled at 150° C. to give 1.04 g of the product 444. 1H NMR (CDCl3) δ 4.21 (q, 2 H), 4.04 (s, 2 H), 1.85-1.45 (m, 8 H), 1.29 (t, 3 H)

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. distillationthe residue vacuum distilled at 150° C.

Sources & evidence

ORD record
ord-42c89541970c460c82e2aa4dc5db327e
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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