Tetrabutylammonium Fluoride → alpha-Ethynylbenzenemethanol

HRID 1588714

反応式

HRID 1588714 の反応式
C[Si]([C:5]#[C:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:6]([CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8])#[CH:5]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 27604161-Phenyl-3-(trimethylsilyl)-2-propyn-1-ol

生成物 1

HCID 20155alpha-Ethynylbenzenemethanol収率 81.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Place a mixture of α-[(trimethylsilyl)ethynyl]-benzene-methanol (4.09 g, 20 mmol) and tetrahydrofuran (25 mL) under argon atmosphere and cool to 0° C. Add, by dropwise addition, tetra-n-butylammonium fluoride (25 mL of a 1M solution in tetrahydrofuran, 25 mmol). Allow to warm to room temperature and stir for 1 hour. Partition between ethyl ether and water. Separate the organic phase, wash with saturated aqueous sodium chloride and concentrate in vacuo. Purify by silica gel chromatography (15% ethyl acetate/hexane) then purify further by distillation to yield 2.15 g of the title compound; bp 100°-110° C. @0.1 mm Hg.

後処理

  1. temperatureAllow to warm to room temperature
  2. customPartition between ethyl ether and water
  3. customSeparate the organic phase
  4. washwash with saturated aqueous sodium chloride
  5. concentrationconcentrate in vacuo
  6. customPurify by silica gel chromatography (15% ethyl acetate/hexane)
  7. distillationthen purify further by distillation

出典と根拠

ORDレコード
ord-3a223550e8214c68a932503169f4d82d
出典データセット
uspto-grants-1993_06
特許番号
US05223518

関連ノート

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