Sodium hydride → 3-(2-Chloro-4-methanesulfonylbenzyl)pentane-2,4-dione

HRID 2266516노트

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HRID 2266516 반응식
[H-].[Na+].[CH3:3][C:4](=[O:9])[CH2:5][C:6](=[O:8])[CH3:7].Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][C:13]=1[Cl:22]>CN(C)C=O.O>[Cl:22][C:13]1[CH:14]=[C:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:16]=[CH:17][C:12]=1[CH2:11][CH:5]([C:4](=[O:9])[CH3:3])[C:6](=[O:8])[CH3:7]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 31261AcetylacetoneHCID 27610831-(Bromomethyl)-2-chloro-4-(methylsulfonyl)benzene

생성물 1

HCID 687834363-(2-Chloro-4-methanesulfonylbenzyl)pentane-2,4-dione

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
5 °C

실험 절차

Sodium hydride (60% in oil, 0.30 g) was added portionwise to a stirred solution of pentane-2,4-dione (0.92 g) in N,N-dimethylformamide (8.0 mL) at 0-10° C. The resulting mixture was stirred at 0-10° C. for 20 minutes and then a solution of 1-bromomethyl-2-chloro-4-methanesulfonylbenzene (2.0 g) in N,N-dimethylformamide (3.0 mL) was added dropwise. The resulting mixture was stirred at room temperature for 5 hours, and then diluted with water and this mixture was extracted with ethyl acetate. The combined extracts were washed with water and saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of ethyl acetate and cyclohexane (1:4 to 3:7 by volume) gave title compound as a white solid, 1.2 g.

후처리

  1. stirringThe resulting mixture was stirred at room temperature for 5 hours
  2. extractionthis mixture was extracted with ethyl acetate
  3. washThe combined extracts were washed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  6. washeluting with a mixture of ethyl acetate and cyclohexane (1:4 to 3:7 by volume)

출처 및 근거

ORD 기록
ord-56875cfe997044d4bfbbd75f7663832e
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858640B2

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