Dimethyl Sulfoxide → 3-(3,4-Dichlorophenyl)-3-methylbutan-2-one

HRID 1627336ノート

反応式

HRID 1627336 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[CH:13]=[C:14]([C:19]([CH3:24])([CH3:23])[CH:20]([OH:22])[CH3:21])[CH:15]=[CH:16][C:17]=1[Cl:18].CCN(CC)CC>C(Cl)Cl.O>[Cl:11][C:12]1[CH:13]=[C:14]([C:19]([CH3:24])([CH3:23])[C:20](=[O:22])[CH3:21])[CH:15]=[CH:16][C:17]=1[Cl:18]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 667400023-(3,4-Dichlorophenyl)-3-methylbutan-2-ol

生成物 1

HCID 212584633-(3,4-Dichlorophenyl)-3-methylbutan-2-one収率 90.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

DMSO (14.7 mL, 205 mmol) was added dropwise to a solution of oxalyl chloride (9.0 mL, 103 mmol) in CH2Cl2 (200 mL) at −78° C. The reaction mixture was stirred for 30 min and a solution of 3-(3,4-dichlorophenyl)-3-methylbutan-2-ol (12 g, 51.4 mmol) in CH2Cl2 (50 mL) was added by cannula over 15 min. After stirring 30 min, Et3N (43 mL, 308 mmol) was added, and the reaction mixture was allowed to warm to room temperature over 1 h. Water (200 mL) was added, and the organic layer was separated. The aqueous layer was further extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography to give 3-(3,4-dichlorophenyl)-3-methylbutan-2-one (10.7 g, 89%). 1H NMR (400 MHz, CDCl3) δ 7.41 (d, 1H), 7.37 (m, 1H), 7.08 (d, 1H), 1.95 (s, 3H), 1.59 (s, 6H).

後処理

  1. stirringAfter stirring 30 min
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was further extracted with CH2Cl2 (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-d368ea0f0fdb46258032f6fc49df01ca
出典データセット
uspto-grants-2014_07
特許番号
US08785488B2

反応ノート

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