Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 3-(3-(benzyloxy)phenyl)-4-methoxybut-2-enoate

HRID 1662579Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=O)[CH2:16][O:17][CH3:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(=[CH:39][C:40]([O:42][CH3:43])=[O:41])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH2:16][O:17][CH3:18])=[CH:39][C:40]([O:42][CH3:43])=[O:41])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 102.A (0.17 g, 0.66 mmol) in benzene (7 mL) was added methyl (triphenylphosphoranylidene)acetate (available from Aldrich) (2.2 g, 6.6 mmol) at room temperature. The mixture was stirred for 72 hours at reflux (100° C.), cooled to room temperature, filtered through silica gel (EtOAc), and concentrated. The crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane) to afford 102.B (mixture of geometric isomers) (0.11 g, 53% yield) as a pale yellow oil.

Workup

temperaturecooled to room temperature
filtrationfiltered through silica gel (EtOAc)
concentrationconcentrated
customThe crude product was purified by silica gel flash chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record: ord-d122901c0d5646748d72138acc89bcb1
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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