Benzaldehyde, p-phenylthio- → Ethyl (E)-3-(4-(phenylthio)phenyl)acrylate

HRID 386441Notes

Reaction equation

HRID 386441 reaction equation
[C:1]1([S:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([O:18][C:19](=[O:35])/[CH:20]=C/C1C=CC(CC2C=CC=CC=2)=CC=1)[CH3:17]>>[C:1]1([S:7][C:8]2[CH:15]=[CH:14][C:11](/[CH:12]=[CH:20]/[C:19]([O:18][CH2:16][CH3:17])=[O:35])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 71023Benzaldehyde, p-phenylthio-HCID 67528407ethyl (E)-3-(4-benzylphenyl)acrylate

Product 1

HCID 86645813Ethyl (E)-3-(4-(phenylthio)phenyl)acrylate

Procedure

The title compound was prepared from 4-(phenylthio)benzaldehyde (S41) and triethylphosphonoacetate using the procedure described for ethyl-(E)-3-(4-benzylphenyl)acrylate (S38). Column chromatography (SiO2, 4×8 cm, 10% EtOAc-hexanes) afforded S42 (1.55 g, 5.5 mmol, 84%) as a yellow oil: 1H NMR (CDCl3, 400 MHz) 9.91 (s, 1H), 7.62 (d, 1H, J=15.8 Hz), 7.46-7.21 (m, 9H), 6.38 (d, 1H, J=15.8 Hz); 13C NMR (CDCl3, 100 MHz) 166.8, 143.6, 140.0, 133.4, 132.7, 132.3, 129.4, 129.1, 128.5, 128.0, 117.8, 60.4, 14.2.

Sources & evidence

ORD record
ord-1efed3474753486cb5090bc766e67498
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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