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

HRID 445833

반응식

HRID 445833 반응식
[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

참가 물질

4

반응물 3

HCID 1140TolueneHCID 10870911Carboxymethylene triphenylphosphoraneHCID 573034645-Hydroxy-[1,1'-biphenyl]-2-carbaldehyde

생성물 1

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

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-b776ab79d0c74eb6beb4ac9bf981ef7f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476308B2

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