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

HRID 2212320ノート

反応式

HRID 2212320 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0134b684204a4aad852425e5d6d6003f
出典データセット
uspto-grants-2006_09
特許番号
US07101911B2

反応ノート

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