Hydrochloric Acid → 3-Cyclopropyl-1-[4-(methylsulphenyl)-phenyl]-propan-1,3-dione

HRID 21453

반응식

HRID 21453 반응식
[CH3:1][C:2]([CH:4]1[CH2:6][CH2:5]1)=[O:3].[H-].[Na+].[CH3:9][S:10][C:11]1[CH:21]=[CH:20][C:14]([C:15](OCC)=[O:16])=[CH:13][CH:12]=1.Cl>O1CCOCC1>[CH:4]1([C:2](=[O:3])[CH2:1][C:15]([C:14]2[CH:20]=[CH:21][C:11]([S:10][CH3:9])=[CH:12][CH:13]=2)=[O:16])[CH2:6][CH2:5]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 13004Cyclopropyl methyl ketoneHCID 24758Sodium hydrideHCID 10130363Ethyl 4-(methylsulphenyl)benzoate

생성물 1

HCID 199317813-Cyclopropyl-1-[4-(methylsulphenyl)-phenyl]-propan-1,3-dione수율 49.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
60 °C

실험 절차

Cyclopropyl methyl ketone (0.84 g) was added to a suspension of sodium hydride (80%, 0.3 g) in dioxane. The mixture was stirred for 20 minutes and ethyl 4-(methylsulphenyl)benzoate (1.0 g) was added. The mixture was stirred and heated at 45° C. for 1.5 hours and at 60° C. for 2 hours. It was left to stand at room temperature overnight. Hydrochloric acid (2M) was added and the mixture was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The flitrate was evaporated to dryness and the residue was purified by chromatography eluted with a mixture of ethyl acetate and hexane to give 3-cyclopropyl-1-[4-(methylsulphenyl)-phenyl]-propan-1,3-dione (0.59 g) as an orange solid, NMR (CDCl3) 1.0(m,2H), 1.2(m,2H), 1.8(m, 1H), 2.5(s,3H), 6.25(s,1H), 7.25(d,2H), 7.8(d,2H), 16.35(bs,1H).

후처리

  1. stirringThe mixture was stirred
  2. waitIt was left
  3. waitto stand at room temperature overnight
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customThe flitrate was evaporated to dryness
  9. customthe residue was purified by chromatography
  10. washeluted with a mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-ff81f5e3b81e4e9384c51fa1f0552849
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424276

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