Tetrabutylammonium Fluoride → 2-Fluoro-5-(4-fluorophenyl)-5-methylhex-1-en-3-ol

HRID 400625노트

반응식

HRID 400625 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[CH2:9][CH:10]=[O:11])=[CH:4][CH:3]=1.[F:14][C:15](C[SiH](C1C=CC=CC=1)C1C=CC=CC=1)=[CH2:16].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:14][C:15]([CH:10]([OH:11])[CH2:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)([CH3:13])[CH3:12])=[CH2:16]

참가 물질

5

반응물 3

HCID 2724141Tetrabutylammonium Fluoride2회HCID 214680123-(4-Fluorophenyl)-3-methylbutyraldehydeHCID 573763252-Fluoroprop-2-enyl(diphenyl)silane

생성물 1

HCID 600266962-Fluoro-5-(4-fluorophenyl)-5-methylhex-1-en-3-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a mixture of 3-(4-fluorophenyl)-3-methylbutyraldehyde (1.2 g, 6.6 mmol) and (1-fluorovinyl)methyldiphenylsilane in 5 mL of THF cooled on ice under nitrogen gas was added 1 mL of TBAF (1 M in THF). The mixture was allowed to warm to room temperature and left overnight. The solvent was evaporated and the residue was taken up in hexanes. The hexane soluble material was fractionated over silica gel (eluent: hexanes to hexanes-ethyl acetate (98:2)) to give a fraction (3.1 g) containing silylated product along with other silanes. This fraction was dissolved in 5 mL of THF and 10 mL of TBAF solution (1 M in THF) was added. The mixture was left at room temperature for 20 minutes, diluted with hexanes-ethyl acetate, and washed with water, dried, filtered, and concentrated in vacuo. Fractionation of the residue over silica gel (eluent: hexanes-ethyl acetate (99:1 to 9:1 gradient)) gave 1.73 g of the crude 2-fluoro-5-(4-fluorophenyl)-5-methylhex-1-en-3-ol as an oil which was used without additional purification.

후처리

  1. temperaturecooled on ice under nitrogen gas
  2. customThe solvent was evaporated
  3. customto give a fraction (3.1 g)
  4. waitThe mixture was left at room temperature for 20 minutes
  5. additiondiluted with hexanes-ethyl acetate
  6. washwashed with water
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-604215ec77cf46f7be9dc5f5379afe03
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

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