Ethyl diazoacetate → (3-Ethoxy-1-ethylpropoxy)acetic acid ethyl ester

HRID 18837Notes

Reaction equation

HRID 18837 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH:6]([OH:9])[CH2:7][CH3:8])[CH3:2].[N+](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:9][CH:6]([CH2:7][CH3:8])[CH2:5][CH2:4][O:3][CH2:1][CH3:2])[CH3:17]

Participants

6

Reactant 2

HCID 12192Ethyl diazoacetateHCID 2945511-Ethoxy-3-pentanol

Product 1

HCID 86023772(3-Ethoxy-1-ethylpropoxy)acetic acid ethyl esterYield 31.8%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 1-ethoxy-3-pentanol (1.32 g, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (1.0 mL, 9.5 mmol). The reaction mixture is stirred at rt for 2 h. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated. The residue is purified by chromatography on silica gel; elution with EtOAc:heptane (1:3) gives 660 mg the product 487.

Workup

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

Sources & evidence

ORD record
ord-af2dc608085941a79ca87a7fd377337e
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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