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

HRID 1646051

反応式

HRID 1646051 の反応式
[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

参加物

8

反応物 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 1230984-(Methylamino)pyridineHCID 15159129(3-Bromophenanthren-9-YL)methanol2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c0a31e0468614ef7807c6bdae9d610f6
出典データセット
uspto-grants-1993_01
特許番号
US05177202

関連ノート

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