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Water → (9R)-4-Chloro-2-(3-hydroxy-3-methylbutoxy)-9-(trifluoromethyl)-9H-fluoren-9-ol

HRID 579386
ノート
印刷プレビュー

反応式

HRID 579386 の反応式
[Cl:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C@@:7]([C:16]([F:19])([F:18])[F:17])([OH:15])[C:6]=2[CH:5]=[C:4]([OH:20])[CH:3]=1.C1(C)C=CC(S(O[CH2:31][CH2:32][C:33]([OH:36])([CH3:35])[CH3:34])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C@@:7]([C:16]([F:18])([F:19])[F:17])([OH:15])[C:6]=2[CH:5]=[C:4]([O:20][CH2:31][CH2:32][C:33]([OH:36])([CH3:35])[CH3:34])[CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 140012952-Methyl-4-[(4-methylbenzenesulfonyl)oxy]butan-2-ol2 回HCID 117599289(9R)-4-Chloro-9-(trifluoromethyl)-9H-fluorene-2,9-diol

生成物 1

HCID 117599101(9R)-4-Chloro-2-(3-hydroxy-3-methylbutoxy)-9-(trifluoromethyl)-9H-fluoren-9-ol収率 69.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
70 °C

実験手順

Under a nitrogen atmosphere, (9R)-4-chloro-9-(trifluoromethyl)-9H-fluorene-2,9-diol (55.5 g) was dissolved in N,N-dimethylformamide (550 ml), 3-hydroxy-3-methylbutyl toluene-4-sulfonate (49.6 g) and potassium carbonate (39.5 g) were added, and the mixture was stirred at an oil bath temperature of 70° C. overnight. To the reaction mixture was added a solution of 3-hydroxy-3-methylbutyl toluene-4-sulfonate (4.0 g) in N,N-dimethylformamide (5 ml), and the mixture was further stirred at the same temperature for 9.5 hr. The reaction mixture was ice-cooled, water (800 ml) was added, and the mixture was extracted with ethyl acetate (900 ml). The obtained organic layer was washed with water (500 ml, 3 times) and saturated brine (500 ml). The obtained organic layer was dried over anhydrous sodium sulfate, the insoluble material was filtered off, and the solvent in the filtrate was evaporated. The obtained residue was purified by silica gel column chromatography (a mixture of hexane and ethyl acetate was used as an elution solvent, first eluted with a mixture of (hexane:ethyl acetate) at a mixing ratio 3:1, and then with the mixture at a mixing ratio 2:1, and further with the mixture at a mixing ratio 3:2) to give the title compound (49.5 g).

後処理

  1. stirringthe mixture was further stirred at the same temperature for 9.5 hr
  2. temperaturecooled
  3. extractionthe mixture was extracted with ethyl acetate (900 ml)
  4. washThe obtained organic layer was washed with water (500 ml, 3 times) and saturated brine (500 ml)
  5. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  6. filtrationthe insoluble material was filtered off
  7. customthe solvent in the filtrate was evaporated
  8. customThe obtained residue was purified by silica gel column chromatography (
  9. additiona mixture of hexane and ethyl acetate
  10. washfirst eluted with a mixture of (hexane:ethyl acetate) at a mixing ratio 3:1

出典と根拠

ORDレコード
ord-60f6f79bf81c456a926931f55abfcff4
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040717B2

反応ノート

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