홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

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

HRID 218258
노트
인쇄 미리보기

반응식

HRID 218258 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+].[Si:21]([O:28][C:29]1[C:36]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])=[C:35]([O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[CH:34]=[CH:33][C:30]=1[CH:31]=O)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].O>C1COCC1>[Si:21]([O:28][C:29]1[C:30](/[CH:31]=[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:33][CH:34]=[C:35]([O:45][Si:46]([C:49]([CH3:50])([CH3:52])[CH3:51])([CH3:48])[CH3:47])[C:36]=1[O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:39])[CH3:40])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 233739753,4,5-Trimethoxybenzylphosphonium bromideHCID 859964842,3,4-Tri(t-butyldimethylsilyloxy)benzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 601306851,2,3-Tri(t-butyldimethylsilyloxy)-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

반응 조건

온도
-70 °C

실험 절차

n-Butyl lithium (0.89 mL, 2.23 mmol, 2.5 M in hexanes) was added dropwise over 10 min to a solution of 3,4,5-trimethoxybenzylphosphonium bromide (0.96 g, 1.83 mmol) in THF (10 mL) at −10° C. The reaction mixture was stirred at this temperature for 15 min then cooled to −70° C. and a solution of 31 (0.93 g, 1.88 mmol) in THF (4 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 (1.5 g). Purification by column chromatography (SiO2; 5:95 TBME:cyclohexane+1% Et3N) gave 32 compound (0.6 g, 50%) as a 86:14 mixture of Z:E isomers:

후처리

  1. temperatureto warm to room temperature
  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 (1.5 g)
  9. customPurification by column chromatography (SiO2; 5:95 TBME:cyclohexane+1% Et3N)

출처 및 근거

ORD 기록
ord-3a768ff6cd5f49368e972ada43b87e03
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08198302B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트