Propargyl alcohol → 3,5-Bis-[(3-hydroxyprop-1-ynyl)]-1-(tert-butyldiphenylsilanyloxymethyl)benzene

HRID 2212320노트

반응식

HRID 2212320 반응식
[CH2:1]([OH:4])[C:2]#[CH:3].[C:5]([Si:9]([O:22][CH2:23][C:24]1[CH:29]=[C:28](Br)[CH:27]=[C:26](Br)[CH:25]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:8])([CH3:7])[CH3:6]>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][CH2:1][C:2]#[C:3][C:26]1[CH:25]=[C:24]([CH2:23][O:22][Si:9]([C:5]([CH3:7])([CH3:6])[CH3:8])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:29]=[C:28]([C:3]#[C:2][CH2:1][OH:4])[CH:27]=1

참가 물질

5

반응물 2

HCID 7859Propargyl alcoholHCID 21964571tert-Butyl-(3,5-dibromobenzyloxy)diphenylsilane

생성물 1

HCID 219645693,5-Bis-[(3-hydroxyprop-1-ynyl)]-1-(tert-butyldiphenylsilanyloxymethyl)benzene수율 88.9%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8471Triethylamine용매

실험 절차

Pd(Ph3P)4 (520 mg), CuBrSMe2 (200 mg) and propargyl alcohol (3.08 ml, 35.1 mmol) are added successively to a solution of tert-butyl-(3,5-dibrombenzyloxy)diphenylsilane (A1, 5.0 g, 9.9 mmol) in triethylamine (50 ml), and the mixture is stirred at RT for 10 min and then under reflux at 80° C. for 2.5 h. After cooling, the reaction mixture is filtered off with suction through kieselguhr, and the filter cake is washed with ethyl acetate (20 ml). The organic phase is concentrated under reduced pressure. Further purification is carried out by chromatography [toluene/acetone (8:2)] on a silica gel column. This gives the title compound (4.0 g) as a colorless solid. TLC, silica gel (glass plates), [toluene/acetone (8:2)], Rf=0.48.

후처리

  1. temperatureunder reflux at 80° C. for 2.5 h
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered off with suction through kieselguhr
  4. washthe filter cake is washed with ethyl acetate (20 ml)
  5. concentrationThe organic phase is concentrated under reduced pressure
  6. customFurther purification

출처 및 근거

ORD 기록
ord-0134b684204a4aad852425e5d6d6003f
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101911B2

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