Propyltriphenylphosphonium bromide → 1-(3,4-Dimethoxyphenyl)-1-(3-ethoxy-4-methoxyphenyl)but-1-ene

HRID 366602

반응식

HRID 366602 반응식
CO[C:3]1[CH:4]=C(C(C2C=CC(OC)=C(OC)C=2)=CC(OC)=O)C=C[C:8]=1OC.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:45]=[CH:46][C:47]=1[O:48][CH3:49])[C:32]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36]([O:42][CH2:43][CH3:44])[CH:35]=1)=O.[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CC.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([C:32]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36]([O:42][CH2:43][CH3:44])[CH:35]=2)=[CH:8][CH2:3][CH3:4])[CH:45]=[CH:46][C:47]=1[O:48][CH3:49]

참가 물질

5

반응물 4

HCID 80374Propyltriphenylphosphonium bromideHCID 2733832Lithium HexamethyldisilazideHCID 9820154Methyl 3,3-bis-(3,4-dimethoxyphenyl)acrylateHCID 222259763,4-Dimethoxy-3'-ethoxy-4'-methoxybenzophenone

생성물 1

HCID 542585151-(3,4-Dimethoxyphenyl)-1-(3-ethoxy-4-methoxyphenyl)but-1-ene

실험 절차

1-(3,4-Dimethoxyphenyl)-1-(3-ethoxy-4-methoxyphenyl)but-1-ene was prepared analogously to methyl 3,3-bis-(3,4-dimethoxyphenyl)acrylate using 3,4-dimethoxy-3'-ethoxy-4'-methoxybenzophenone (1 g, 3.2 mmol), propyltriphenylphosphonium bromide (1.34 g, 3.5 mmol) and lithium hexamethyldisilazide (2.7 mL, 3.5 mmol, 1.3M) with a reaction time of 2.5 hours at room temperature. The crude mixture was purified by chromatography (silica gel, methylene chloride) followed by a Kugekrohr distillation to yield 0.77 g (71%) of a mixture of the E and Z isomers as an oil: H NMR (CDCl3) δ 6.92-6.65 (m, 12 H), 6.02-5.89 (m, 2 H), 4.12-3.96 (m, 4 H), 3.92 (s, 3 H), 3.91 (s, 3 H), 3.86 (s, 3 H), 3.85 (s, 3 H), 3.82 (s, 3 H), 3.81 (s, 3 H), 2.22-2.04 (m, 4 H), 1.51-1.38 (m, 6 H), 1.14-0.98 (m, 6 H); 13C NMR (CDCl3) δ 148.5, 148.1, 147.8, 147.7, 140.4, 140.4, 136.0, 135.9, 133.0, 132.9, 130.1, 130.0, 122.2, 119.8, 114.6, 113.1, 112.0, 111.0, 110.7, 110.4, 64.3, 64.2, 55.9, 23.2, 14.8, 14.7; Anal. Calcd for C21H26O4. Theoretical: C, 73.66; H, 7.65. Found: C, 73.32; H, 7.26.

후처리

  1. customwith a reaction time of 2.5 hours
  2. customat room temperature
  3. customThe crude mixture was purified by chromatography (silica gel, methylene chloride)
  4. distillationfollowed by a Kugekrohr distillation

출처 및 근거

ORD 기록
ord-1595e5402a83446a986dcb8c0e535322
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130226

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