(2-(Dimethylamino)ethyl)triphenylphosphonium bromide → (E)-3-{6-[3-Dimethylamino-1-(4-tolyl)prop-1E-enyl]-2-pyridyl}acrylic acid

HRID 638645

반응식

HRID 638645 반응식
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([C:7]([C:9]2[N:14]=[C:13](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])[CH:12]=[CH:11][CH:10]=2)=O)=[CH:3][CH:2]=1.[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])C=CC=CC=1>>[CH3:32][N:31]([CH3:33])[CH2:30]/[CH:29]=[C:7](/[C:9]1[N:14]=[C:13](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])[CH:12]=[CH:11][CH:10]=1)\[C:4]1[CH:5]=[CH:6][C:1]([CH3:20])=[CH:2][CH:3]=1

참가 물질

3

반응물 2

HCID 2724136(2-(Dimethylamino)ethyl)triphenylphosphonium bromideHCID 119712602-Propenoic acid, 3-[6-(4-methylbenzoyl)-2-pyridinyl]-, (E)-

생성물 1

HCID 13191753(E)-3-{6-[3-Dimethylamino-1-(4-tolyl)prop-1E-enyl]-2-pyridyl}acrylic acid

실험 절차

Treatment of (E)-3-[6-(4-toluoyl)-2-pyridyl]acrylic acid, vide supra, with the Wittig reagent derived from triphenyldimethylaminoethylphosphonium bromide by the method of example 1 gave a mixture of isomeric acids which were separated by fractional crystallization from ethyl acetate. The less-soluble E-isomer, (E)-3-{6-[3-dimethylamino-1-(4-tolyl)prop-1E-enyl]-2-pyridyl}acrylic acid was purified by crystallization from isopropanol, m.p. 222°-225° (decomp.)

후처리

  1. customgave
  2. additiona mixture of isomeric acids which
  3. customwere separated by fractional crystallization from ethyl acetate
  4. customThe less-soluble E-isomer, (E)-3-{6-[3-dimethylamino-1-(4-tolyl)prop-1E-enyl]-2-pyridyl}acrylic acid was purified by crystallization from isopropanol, m.p. 222°-225° (decomp.)

출처 및 근거

ORD 기록
ord-8d3ddce9407f402e84abec22115d5459
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04562258

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