Ethyl diazoacetate → HCID 45098996, compound

HRID 2053615Notes

Reaction equation

HRID 2053615 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, 2H), 4.09 (d, 2H), 3.25-3.15 (m, 1H), 2.00-1.78 (m, 2H), 1.75-1.35 (m, 6H), 1.29 (t, 3H), 1.15 (d, 3H)

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-79efbe69c7f14c9c89d958e1be471551
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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