Tetrabutylammonium Fluoride → alpha-Ethynylbenzenemethanol

HRID 1588714

반응식

HRID 1588714 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 20155alpha-Ethynylbenzenemethanol수율 81.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3a223550e8214c68a932503169f4d82d
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05223518

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