2-(Cyclopent-1-en-1-yl)-4-fluoro-1-methoxybenZene → 2-Cyclopentyl-4-fluoro-1-methoxybenzene

HRID 471920Notes

Reaction equation

HRID 471920 reaction equation
[C:1]1([C:6]2[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH:2]=1>[Pd].CO>[CH:1]1([C:6]2[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 593949342-(Cyclopent-1-en-1-yl)-4-fluoro-1-methoxybenZene

Product 1

HCID 674570262-Cyclopentyl-4-fluoro-1-methoxybenzeneYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a flask charged with 2-cyclopentenyl-4-fluoro-1-methoxybenzene (1500 mg, 4.68 mmol) and 10% Pd/C (50 mg) under inert atmosphere was added methanol. The reaction was stirred under H2 atmosphere for 16 h, then filtered and concentrated. Purification by silica gel chromatography (0-30% ethyl acetate/hexanes) provided 2-cyclopentyl-4-fluoro-1-methoxybenzene (800 mg, 88% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 6.96 (dd, J=3.0, 9.9 Hz, 1H), 6.88-6.76 (m, 2H), 3.83 (s, 3H), 3.35 (q, J=8.5 Hz, 1H), 2.09-2.01 (m, 2H), 1.86-1.66 (m, 4H), 1.59-1.50 (m, 2H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (0-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b1d7559987d440ba9e6335ccb15366da
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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