3-Ethoxycyclohept-2-en-1-one → 3-Phenethylcycloheptenone

HRID 1006185Notes

Reaction equation

HRID 1006185 reaction equation
[CH2:1]([O:3][C:4]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6](=[O:11])[CH:5]=1)[CH3:2].[CH2:12]([Mg]Cl)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6](=[O:11])[CH:5]=1)[CH3:2].[CH2:12]([C:4]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6](=[O:11])[CH:5]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 156706513-Ethoxycyclohept-2-en-1-oneHCID 178418865HCID 178418865, compound

Product 2

HCID 113563453-PhenethylcycloheptenoneYield 184.8%HCID 156706513-Ethoxycyclohept-2-en-1-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Ethoxycycloheptenone was synthesized following published procedures.8 The general procedure for the preparation of substrates using 3-ethoxycycloheptenone (766 mg, 4.97 mmol) and phenethymagnesium chloride (10 mmol, 1M in THF) gave, after flash chromatography (4:1 hexanes:ethyl acetate), the title compound as a colorless liquid (0.984 g, 93%). 1H NMR (300 MHz, CDCl3): δ 7.32-7.13 (m, 5H), 5.91 (br s, 1H), 2.79 (dd, J=10.5, 7.8 Hz, 2H), 2.64-2.39 (m, 6H), 1.86-1.70 (m, 4H). 13C NMR (75 MHz, CDCl3): δ 204.0, 161.1, 140.9, 129.6, 128.5, 128.3, 126.3, 43.0, 42.4, 34.4, 33.1, 25.4, 21.5. IR (neat): 3027, 2937, 2865, 1656, 1495, 1453, 1268, 878, 747, 699 cm−1.

Workup

  1. customfor the preparation of substrates
  2. customgave

Sources & evidence

ORD record
ord-247405f8be084eb09b22862624015f88
Source dataset
uspto-grants-2004_09
Patent number
US06787655B2

Reaction notes

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