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

HRID 400630

反応式

HRID 400630 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9cdcad5474b1446cbfeac0a9d9ddc0cf
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

関連ノート

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