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

HRID 1084311노트

반응식

HRID 1084311 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.C(OCC)C>C(Cl)Cl.C1COCC1.CN(C)C1C=CN=CC=1>[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 3283Diethyl EtherHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 15159129(3-Bromophenanthren-9-YL)methanol2회

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 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-dimethylaminopyridine (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-79c064786a4246e0b200c92ff3acdd34
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05004739

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