Toluene → (E)-ethyl 3-(5-hydroxy-[1,1'-biphenyl]-2-yl)acrylate

HRID 1909548

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([CH:14]=O)=[CH:4][CH:3]=1.[C:16]([CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:18])=[O:17].[C:39]1(C)C=CC=C[CH:40]=1>>[OH:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:14]=[CH:19]/[C:16]([O:18][CH2:39][CH3:40])=[O:17])=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=1

Participants

Reactant 3

HCID 1140Toluene

HCID 10870911Carboxymethylene triphenylphosphorane

HCID 573034645-Hydroxy-[1,1'-biphenyl]-2-carbaldehyde

Product 1

HCID 58566652(E)-ethyl 3-(5-hydroxy-[1,1'-biphenyl]-2-yl)acrylate

Procedure

A solution of 5-hydroxy-[1,1′-biphenyl]-2-carbaldehyde (651) (292 mg, 1.47 mmol) and (carboxymethylene)-triphenylphosphorane (564.5 mg, 1.62 mmol) in toluene (15 mL) was refluxed for 24 hours. The reaction was concentrated in vacuo and was purified by flash column chromatography on silica gel with hexanes and EtOAc (30%) to give (E)-ethyl 3-(5-hydroxy-[1,1′-biphenyl]-2-yl)acrylate (652).

Workup

concentrationThe reaction was concentrated in vacuo
customwas purified by flash column chromatography on silica gel with hexanes and EtOAc (30%)

Sources & evidence

ORD record: ord-fbe773790a124d9987d1933f8f5716e3
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598374B2

Linked notes

Loading…