Methyl 2-allyl-2-phenyl-4-pentenoate → Methyl 2-phenyl-2-propylpentanoate

HRID 494435Notes

Reaction equation

[CH2:1]([C:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH2:9][CH:10]=[CH2:11])[C:5]([O:7][CH3:8])=[O:6])[CH:2]=[CH2:3]>C(OCC)(=O)C.[Pd]>[C:12]1([C:4]([CH2:9][CH2:10][CH3:11])([CH2:1][CH2:2][CH3:3])[C:5]([O:7][CH3:8])=[O:6])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of the product of Example 1A (7.5 g, 32.61 mmol) in ethyl acetate (125 mL) was treated with 10% palladium on carbon (600 mg) and stirred at 25° C. under hydrogen gas for 18 hours. The solution was filtered through Celite® and the filtrate was concentrated in vacuo to give the title compound (7.63 g, 100%). 1H NMR (300 MHz, CDCl3): δ 7.27 (m, 5 H), 3.64 (m, 3 H), 1.96 (m, 4 H), 1.08 (m, 4 H), 0.89 (t, J=7.17 Hz, 6 H).

Workup

filtrationThe solution was filtered through Celite®
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-2e16aba769f441d2b0e0d965dd200900
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538105B2

Reaction notes

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