Ethyl diazoacetate → HCID 45098996, compound

HRID 18824Notes

Reaction equation

HRID 18824 reaction equation
[CH:1]1([CH:6]([OH:8])[CH3:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][O:8][CH:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:7])[CH3:16]

Participants

6

Reactant 2

HCID 12192Ethyl diazoacetateHCID 954341-Cyclopentylethanol

Product 1

HCID 45098996HCID 45098996, compoundYield 44.8%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 1-cyclopentylethan-1-ol (1.14 g, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.03 mmol). The reaction mixture is stirred at rt for 0.5 h. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue is purified by chromatography on silica gel; elution with EtOAc:heptane (1:9) gives 0.81 g of the product 452. 1H NMR (CDCl3) δ 4.30-4.15 (m, 2 H), 4.09 (d, 2 H), 3.25-3.15 (m, 1 H), 2.00-1.78 (m, 2 H), 1.75-1.35 (m, 6 H), 1.29 (t, 3 H), 1.15 (d, 3 H).

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. customthe residue is purified by chromatography on silica gel
  4. washelution with EtOAc:heptane (1:9)

Sources & evidence

ORD record
ord-4fff985c247c489884ef37c5ad713465
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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