HCID 86758778, compound → HCID 86758780, compound

HRID 1633828Notes

Reaction equation

HRID 1633828 reaction equation
[OH:1][CH2:2][CH:3]1[CH:5]([CH:6]=[CH2:7])[CH:4]1[C:8]([O:10][CH2:11][CH3:12])=[O:9]>[Pd].CO>[CH2:6]([CH:5]1[CH:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]1[CH2:2][OH:1])[CH3:7]

Participants

4

Reactant 1

HCID 86758778HCID 86758778, compound

Product 1

HCID 86758780HCID 86758780, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of a mixture of ethyl (1SR,2SR,3RS)-2-hydroxymethyl-3-vinylcyclopropane carboxylate (500 mg, 2.94 mmol) and 5% palladium on carbon (70-mg) in methanol (25 mL) was stirred under hydrogen atmosphere overnight. The catalyst was then filtered off through celite and the solvent was removed under vacuo. The residue was purified by column chromatography using ethyl acetate and hexane 1:2 as eluent to give 380 mg (80% yield) of ethyl (1SR,2SR,3RS)-3-ethyl-2-hydroxymethylcyclopropane carboxylate.

Workup

  1. filtrationThe catalyst was then filtered off through celite
  2. customthe solvent was removed under vacuo
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ea04391b12724c7fb0779a364b76d0f3
Source dataset
uspto-grants-2003_01
Patent number
US06504052B1

Reaction notes

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