Sodium hydride → 5-Chloro-7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran

HRID 400657ノート

反応式

HRID 400657 の反応式
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[Cl:9][C:10]1[CH:11]=[C:12]([C:19]([CH3:28])([CH3:27])[CH2:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[C:13]2[O:17][CH2:16][CH2:15][C:14]=2[CH:18]=1>CS(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([C:19]([CH3:28])([CH3:27])[CH2:20][C:21]2([C:22]([F:23])([F:24])[F:25])[CH2:2][O:26]2)[C:13]2[O:17][CH2:16][CH2:15][C:14]=2[CH:18]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 469392144-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one

生成物 1

HCID 600263575-Chloro-7-[1,1-dimethyl-2-(2-trifluoromethyloxiranyl)ethyl]-2,3-dihydrobenzofuran収率 91.1%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

To a solution of trimethylsulfoxonium iodide (343 mg, 1.56 mmol) in 3 mL of anhydrous DMSO was treated with NaH (60% in mineral oil, 66.0 mg, 1.65 mmol) in portions and the mixture was stirred at room temperature for 30 minutes. The mixture was transferred to a solution of 4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one (400 mg, 1.30 mmol) in 1 mL of anhydrous DMSO over 5 minutes and the resulting mixture was stirred overnight. The mixture was quenched with water and extracted with three 20 mL portions of ethyl acetate. The combined organic layers were washed with two 5 mL portions of water, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 380 mg (91% yield) of the title product as a yellow oil. The crude product was sufficiently pure and used without further purification.

後処理

  1. stirringthe resulting mixture was stirred overnight
  2. customThe mixture was quenched with water
  3. extractionextracted with three 20 mL portions of ethyl acetate
  4. washThe combined organic layers were washed with two 5 mL portions of water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6d38df95cc6546d59c8767e119742b63
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

反応ノート

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