Cyclopropyl methyl ketone → 1-[4-Bromo-2-(methylsulphenylmethyl)phenyl]-3-cyclopropylpropan-1,3-dione

HRID 863399노트

반응식

HRID 863399 반응식
[CH3:1][C:2]([CH:4]1[CH2:6][CH2:5]1)=[O:3].[Br:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[C:10]([CH2:18][S:19][CH3:20])[CH:9]=1.[H-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[Br:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](=[O:13])[CH2:1][C:2]([CH:4]2[CH2:6][CH2:5]2)=[O:3])=[C:10]([CH2:18][S:19][CH3:20])[CH:9]=1

참가 물질

6

반응물 4

HCID 13004Cyclopropyl methyl ketoneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 18978023Methyl 4-bromo-2-((methylthio)methyl)benzoate

생성물 1

HCID 189780111-[4-Bromo-2-(methylsulphenylmethyl)phenyl]-3-cyclopropylpropan-1,3-dione수율 52.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of cyclopropyl methyl ketone (1.1 g) and methyl 4-bromo-2-(methylsulphenylmethyl)benzoate (3.6 g ) in tetrahydrofuran was added to a refluxing suspension of sodium hydride (80%, 0.9 g) in tetrahydrofuran. After the addition was complete, the mixture was maintained at reflux temperature for 30 minutes. It was then cooled and poured onto 100 g of ice and 50 ml of saturated aqueous sodium bicarbonate. The mixture was extracted with hexane, the organic solution dried (anhydrous sodium sulphate) and the solvent evaporated to give 1-[4-bromo-2-(methylsulphenylmethyl)phenyl]-3-cyclopropylpropan-1,3-dione as an orange oil (2.23 g), NMR (CDCl3): 1.00(2H, m), 1.20(2H, m), 1.75(1H, m), 2.03(3H, s), 3.92(2H, s), 6.00(1H, s), 7.35(1H, m), 7.45(1H, m), 7.58(1H, m) 14.74(1H, s).

후처리

  1. additionAfter the addition
  2. temperaturethe mixture was maintained
  3. temperatureat reflux temperature for 30 minutes
  4. temperatureIt was then cooled
  5. extractionThe mixture was extracted with hexane
  6. dry with materialthe organic solution dried (anhydrous sodium sulphate)
  7. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-25995897a1334ab2873c2d6875997a50
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05721193

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