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Potassium Carbonate → (R)-5-Chloro-7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)-ethyl]-2,3-dihydrobenzofuran

HRID 854170
ノート
印刷プレビュー

反応式

HRID 854170 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:29])([CH3:28])[CH2:12][C@:13]([CH2:19]SC2C=CC(C)=CC=2)([OH:18])[C:14]([F:17])([F:16])[F:15])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.F[B-](F)(F)F.C[O+](C)C.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>ClCCl.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:28])([CH3:29])[CH2:12][C@:13]2([C:14]([F:17])([F:15])[F:16])[CH2:19][O:18]2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 69419561(S)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol

生成物 1

HCID 11638349(R)-5-Chloro-7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)-ethyl]-2,3-dihydrobenzofuran収率 95%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol (1.43 g, 3.21 mmol) in 10 mL of anhydrous dichloromethane was added trimethyloxonium tetrafluoroborate (713 mg, 4.82 mmol). The resulting suspension was stirred at room temperature for 4.5 hours. A solution of potassium carbonate (1.33 g, 9.64 mmol) in 10 mL of water was then added. After 13 hours, the reaction mixture was poured into 40 mL of saturated aqueous sodium bicarbonate solution and extracted with three 50 mL portions of dichloromethane. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by column chromatography with silica gel (eluted with 0%-2% EtOAc/hexanes) afforded the title compound as a clear oil (974 mg, 95%).

後処理

  1. waitAfter 13 hours
  2. extractionextracted with three 50 mL portions of dichloromethane
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography with silica gel (eluted with 0%-2% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-899c0cdea39447fc91ae5270a8c98a3f
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07256300B2

反応ノート

読み込み中…

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