3-Ethoxycyclopent-2-en-1-one → 3-Benzylcyclopent-2-en-1-one

HRID 991960Notes

Reaction equation

HRID 991960 reaction equation
C(O[C:4]1[CH2:8][CH2:7][C:6](=[O:9])[CH:5]=1)C.[CH2:10]([Mg]Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([C:4]1[CH2:8][CH2:7][C:6](=[O:9])[CH:5]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 897773-Ethoxycyclopent-2-en-1-oneHCID 178418336HCID 178418336, compound

Product 1

HCID 118299173-Benzylcyclopent-2-en-1-one

Procedure

The general procedure for the preparation of substrates using 3-ethoxycyclopentenone (0.88 g, 7.0 mmol) and benzylmagnesium chloride (10 mmol, 1 M in diethyl ether) gave, after flash chromatography (2:1 hexanes:ethyl acetate) and Kugelrohr distillation (0.4 torr, 200° C.), the title compound as a white solid (0.58 g, 50%). m.p. 32-33° C. Spectroscopic data were consistent with previously reported data for this compound.3

Workup

  1. customThe general procedure for the preparation of substrates
  2. customgave
  3. distillationafter flash chromatography (2:1 hexanes:ethyl acetate) and Kugelrohr distillation (0.4 torr, 200° C.)

Sources & evidence

ORD record
ord-0ce265038eb84221804a23b430c5d4e9
Source dataset
uspto-grants-2002_10
Patent number
US06465664B1

Reaction notes

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