Triethylamine → [(3-Bromophenanthren-9-YL)methoxy](tert-butyl)dimethylsilane

HRID 1646051

반응식

HRID 1646051 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[C:7]([CH2:16][OH:17])[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(N(CC)CC)C.CNC1C=CN=CC=1>C(Cl)Cl.C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[C:7]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 1230984-(Methylamino)pyridineHCID 15159129(3-Bromophenanthren-9-YL)methanol2회

생성물 1

HCID 15159130[(3-Bromophenanthren-9-YL)methoxy](tert-butyl)dimethylsilane수율 87%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-bromo-9-(hydroxymethyl) phenanthrene, 4 (5.96 g, 20.8 mmol) and t-butyldimethylsilyl chloride (4.7 g, 31 mmol) in 100 ml of CH2Cl2 and 20 ml of THF was added triethylamine (4.9 ml, 35 mmol) followed by 4-methylaminopyridine (250 mg, 2.05 mmol). After stirring at room temperature for 20 hours, the solution was poured into 300 ml of ethyl ether and washed successively with sat. NH4Cl, sat. NaHCO3, H2O, and brine. Drying (Na2SO4) and evaporation gave a brown solid which was purified by flash chromatography through 400 g of silica gel (1:4 CH2Cl2 -hexane) to yield 7.23 g (87%) of the title compound as a pale yellow solid.

후처리

  1. washwashed successively with sat. NH4Cl, sat. NaHCO3, H2O, and brine
  2. customDrying
  3. custom(Na2SO4) and evaporation
  4. customgave a brown solid which
  5. customwas purified by flash chromatography through 400 g of silica gel (1:4 CH2Cl2 -hexane)

출처 및 근거

ORD 기록
ord-c0a31e0468614ef7807c6bdae9d610f6
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05177202

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