Sodium hydride → 4-(3-Fluorophenyl)-2,2-dimethyl-5-(4-(methylthio)phenyl)furan-3(2H)-one

HRID 2298315노트

반응식

HRID 2298315 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[C:22]([CH3:28])([CH3:27])[C:23](C#N)=[O:24]>C1COCC1>[CH3:27][C:22]1([CH3:28])[C:23](=[O:24])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)[O:10]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 118178202-(3-Fluorophenyl)-1-(4-(methylthio)phenyl)ethanoneHCID 124878382-Bromo-2-methylpropanoyl cyanide

생성물 1

HCID 183855844-(3-Fluorophenyl)-2,2-dimethyl-5-(4-(methylthio)phenyl)furan-3(2H)-one수율 80.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of 2-(3-fluorophenyl)-1-{4-(methylthio)phenyl}-ethan-1-one (100 g) in 1 L dry THF, was added portion-wise 26 g of 95 % sodium hydride at 0° C. The reaction solution was stirred at the same temperature for 1 hour. Then 69 g of α-bromo-isobutyryl cyanide diluted in 25 ml dry THF was added dropwise to the stirred solution at 0° C. The reaction mixture was stirred overnight while allowing to warm gradually to room temperature. The solution was concentrated in vacuo, to which was added 50 ml water. The aqueous solution was extracted with ethylacetate (1 L). The organic layer was concentrated in vacuo and purified by column chromatography (hexane/ethylacetate=6:1) to give 102 g of 2,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylthio)phenyl}-3(2H)-furanone. mp: 106° C. NMR: δ1.55 (s, 6H), 2.50 (s. 3H), 6.97-7.11 (m, 3H), 7.18 (d, J=9.0 Hz, 2H), 7.26-7.36 (m, 1H), 7.55 (d, J=9.0 Hz, 2H).

후처리

  1. additionwas added dropwise to the stirred solution at 0° C
  2. stirringThe reaction mixture was stirred overnight
  3. concentrationThe solution was concentrated in vacuo, to which
  4. additionwas added 50 ml water
  5. extractionThe aqueous solution was extracted with ethylacetate (1 L)
  6. concentrationThe organic layer was concentrated in vacuo
  7. custompurified by column chromatography (hexane/ethylacetate=6:1)

출처 및 근거

ORD 기록
ord-b434d05ade254b1c99dbafdb415a9deb
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06492416B1

반응 노트

불러오는 중…