Water → 1,2-Di(t-butyldimethylsilyloxy)-3-ethoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene

HRID 218261노트

반응식

HRID 218261 반응식
C([Li])CCC.[Br-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:19][CH3:20])[C:16]=1[O:17][CH3:18])[CH2:12][PH3+].[CH2:21]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[C:26]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C:25]=1[O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[CH3:22].O>C1COCC1>[Si:33]([O:32][C:26]1[C:27](/[CH:28]=[CH:12]\[C:11]2[CH:10]=[C:9]([O:8][CH3:7])[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:30][CH:31]=[C:24]([O:23][CH2:21][CH3:22])[C:25]=1[O:40][Si:41]([C:44]([CH3:45])([CH3:47])[CH3:46])([CH3:42])[CH3:43])([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]

참가 물질

6

반응물 4

HCID 962WaterHCID 233739753,4,5-Trimethoxybenzylphosphonium bromideHCID 859964854-Ethoxy-2,3-di(t-butyldimethylsilyloxy)benzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 601306911,2-Di(t-butyldimethylsilyloxy)-3-ethoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene수율 34%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

n-Butyl lithium (0.85 mL, 1.36 mmol, 1.6 M in hexanes) was added dropwise over 10 min to a solution of 3,4,5-trimethoxybenzylphosphonium bromide (0.58 g, 1.12 mmol) in THF (7 mL) at −10° C. The reaction mixture was stirred at this temperature for 15 min then cooled to −70 C and a solution of 35 (0.47 g, 1.14 mmol) in THF (3 mL) was added and the reaction mixture was allowed to warm to room temperature with stirring overnight. The reaction mixture was cooled to 0° C. and water was added. The reaction mixture was extracted with TBME (3×) and the organic phase was washed successively with water and brine, dried (Na2SO4) and concentrated in vacuo to give crude product (0.67 g). Purification by column chromatography (SiO2 2:98 EtOAc:cyclohexane+1% Et3N) gave 36 (0.21 g, 34%) as an 89:11 mixture of Z:E isomers.

후처리

  1. temperaturethen cooled to −70 C
  2. stirringwith stirring overnight
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. extractionThe reaction mixture was extracted with TBME (3×)
  5. washthe organic phase was washed successively with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto give crude product (0.67 g)
  9. customPurification by column chromatography (SiO2 2:98 EtOAc:cyclohexane+1% Et3N)

출처 및 근거

ORD 기록
ord-bc7cbebff0c643d29402b9c53bd0a05c
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198302B2

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