cis-Cinnamaldehyde → (2S)-4-phenylbut-3-en-2-ol

HRID 883740Notes

Reaction equation

[Zn](C)[CH3:2].[CH:4](=[O:13])/[CH:5]=[CH:6]\[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[C:7]1([CH:6]=[CH:5][C@@H:4]([OH:13])[CH3:2])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Reactant 2

HCID 6428995cis-Cinnamaldehyde

HCID 178477796HCID 178477796, compound

Product 1

HCID 54548709(2S)-4-phenylbut-3-en-2-olYield 91%

Procedure

The product was prepared by General procedure M using 4.5 mg (0.012 mmol) ligand 2, 0.30 mL (0.60 mmol, 2.0 M in hexanes) Me2Zn, 116 μL (0.30 mmol) Ti(OtBu)4, and 19 μL (0.15 mmol) cis-cinnamaldehyde. The crude product was purified by column chromatography on silica (10% ethyl acetate in hexanes) to afford the title compound as a colorless oil in 91% yield (20 mg, 0.14 mmol). 1H NMR (CDCl3, 500 MHz) δ. □ □□ (d, 3H, J=6.2 Hz), 1.66 (br s, 1H), 4.69 (dq, 1H, J=8.5, 6.4 Hz), 5.60 (dd, 1H, J=11.5, 9.3 Hz), 6.40 (d, 1H, J=11.6 Hz), 7.18 (d, 2H, J=7.4 Hz), and 7.25 (t, 3H, J=7.5 Hz) ppm; 13C{1H} NMR (CDCl3, 125 MHz) δ.23.6, 64.1, 127.2, 128.3, 128.8, 130.0, 135.7, and 136.7 ppm; 1H NMR and 13C NMR spectra for this compound compare with previously reported literature data.

Workup

customThe product was prepared by General procedure M
customThe crude product was purified by column chromatography on silica (10% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-b9dc3a05434e443b979f30d2b0f55d26
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236976B2

Reaction notes

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