Cesium fluoride → 2-Fluoro-5-(5-fluoro-2-methoxyphenyl)-5-methylhex-1-en-3-ol

HRID 400630

반응식

HRID 400630 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([C:8]([CH3:13])([CH3:12])[CH2:9][CH:10]=[O:11])[CH:7]=1.[F:16][C:17]([Si](C)(C)C1C=CC=CC=1)=[CH2:18].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F-].[Cs+]>C1COCC1.C(OCC)(=O)C.C(O)(=O)C.O>[F:16][C:17]([CH:10]([OH:11])[CH2:9][C:8]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:14][CH3:15])([CH3:12])[CH3:13])=[CH2:18]

참가 물질

9

반응물 4

HCID 25953Cesium fluorideHCID 2724141Tetrabutylammonium FluorideHCID 578098963-(5-Fluoro-2-methoxyphenyl)-3-methylbutyraldehydeHCID 60026366(1-Fluorovinyl)dimethylphenylsilane

생성물 1

HCID 600266102-Fluoro-5-(5-fluoro-2-methoxyphenyl)-5-methylhex-1-en-3-ol수율 59.9%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-(5-fluoro-2-methoxyphenyl)-3-methylbutyraldehyde (1.1 g, 5.2 mmol) and the above (1-fluorovinyl)dimethylphenylsilane (2.2 g, 12.2 mmol) in 5 mL of THF was added 0.6 mL of tetrabutylammonium fluoride (1 M in THF) and the mixture was stirred at room temperature overnight. TLC showed partial conversion to product. Cesium fluoride (0.22 g) was added and the mixture was stirred at room temperature for 3 days. 2 mL of water and 2 mL of acetic acid were added and the mixture was warmed at 60° C. for 2 hours to effect desilylation of any silylated product. The mixture was diluted with ethyl acetate, washed with water, dried, filtered and concentrated in vacuo. Fractionation of the residue over silica gel (eluent: hexanes-dichloromethane (3:1 to 1:3 gradient) gave 0.798 g (59.5% yield) of 2-fluoro-5-(5-fluoro-2-methoxyphenyl)-5-methylhex-1-en-3-ol as an oil which was used without additional purification.

후처리

  1. stirringthe mixture was stirred at room temperature for 3 days
  2. temperaturethe mixture was warmed at 60° C. for 2 hours
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9cdcad5474b1446cbfeac0a9d9ddc0cf
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

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