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Methyl trifluoromethyl ketone → 1,1,1-Trifluoro-2-methyl-3-(4-phenylsulfonylphenoxy)propan-2-ol

HRID 35880
ノート
印刷プレビュー

反応式

HRID 35880 の反応式
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[F:9][C:10]([F:15])([F:14])[C:11](=[O:13])[CH3:12].[C:16]1([S:22]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CS(C)=O.O1CCCC1.O>[F:9][C:10]([F:15])([F:14])[C:11]([CH3:2])([OH:13])[CH2:12][O:31][C:28]1[CH:27]=[CH:26][C:25]([S:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:23])=[O:24])=[CH:30][CH:29]=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

8

反応物 4

HCID 9871Methyl trifluoromethyl ketoneHCID 24758Sodium hydride2 回HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 3438044-(Benzenesulfonyl)phenol

生成物 1

HCID 199393161,1,1-Trifluoro-2-methyl-3-(4-phenylsulfonylphenoxy)propan-2-ol収率 9.5%

試薬・触媒・溶媒 3

HCID 679
Dimethyl Sulfoxide
溶媒
2 回
HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
10 °C

実験手順

A suspension of trimethylsulfoxonium iodide (1.6 6 g, 7.56 mmol) and sodium hydride (0.36 g, 7.56 mmol of 50% in oil) was stirred in 25 mL of dimethylsulfoxide for 25 minutes. The mixture was cooled to 10° C. and was treated with a solution of trifluoroacetone (0.72 g, 6.41 mmol) in tetrahydrofuran (3 mL). After stirring for 20 minutes, the solution was allowed to warm to room temperature where it was treated with a solution of 4-(phenylsulfonyl)phenol (1.5 g, 6.40 mmol) and sodium hydride (0.31 g, 6.4 .mmol of 50% in oil) in dimethylsulfoxide (7.5 mL). The mixture was stirred for 1 hour and then heated to 50° C. for 18 hours. The reaction was poured into water, acidified to pH 6, and extracted with diethylether. The combined organic fractions were evaporated to give an oil. Chromatography, eluting with dichloromethane yielded the title compound as a tan solid (0.22 g); mp 94°-96° C.; NMR: 1.39 (s,3, CH3), 4.12 (q,2, CH2), 6.39 (s,1, OH), 7.17 (s,1, Ar), 7.20 (s,1, Ar), 7.63 (m,3, Ar), 7.91 (m,4, Ar); MS: m/z=361(M+1). Analysis for C16H15F3O4S: Calculated: C, 53.33; H, 4.20; Found: C, 53.54: H, 4.25.

後処理

  1. temperatureto warm to room temperature where it
  2. stirringThe mixture was stirred for 1 hour
  3. temperatureheated to 50° C. for 18 hours
  4. extractionextracted with diethylether
  5. customThe combined organic fractions were evaporated
  6. customto give an oil
  7. washChromatography, eluting with dichloromethane

出典と根拠

ORDレコード
ord-ec5b7bac7a3c49c0a56de6b59478deb2
出典データセット
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05411973

反応ノート

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