Water → 3-Benzoylpyrrole

HRID 327843노트

반응식

HRID 327843 반응식
[H-].[Na+].[C:3]1([C:9]([CH:11]=[CH2:12])=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S([CH2:23][N+:24]#[C-:25])(C1C=CC(C)=CC=1)(=O)=O.[OH2:26]>C(OCC)C.CS(C)=O>[C:9]([C:11]1[CH:12]=[CH:25][NH:24][CH:23]=1)(=[O:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 130281-Phenyl-2-propen-1-oneHCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanide

생성물 1

HCID 27732343-Benzoylpyrrole

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 3283Diethyl Ether용매3회

실험 절차

To a stirred suspension of sodium hydride (8.0 g) in 200 ml of dry ethyl ether was added dropwise a solution of phenylvinylketone (13.22 g) and tosylmethyl isocyanide (19.52) in 150 ml of dry methyl sulfoxide and 300 ml of dry ethyl ether at such a rate that the ether refluxed gently. After complete addition, the suspension was stirred at room temperature for 30 minutes and subsequently hydrolyzed by dropwise addition of 200 ml of water. The ether layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, 0.1N sulfuric acid, and again with water. The organic phase was dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1). The desired fractions were concentrated and the residual oil was crystallized from DCM/hexane, affording the product as crystals (7.11 g), m.p. 98°-99° C. (lit* m.p. 96°-97° C.).

후처리

  1. temperaturerefluxed gently
  2. additionAfter complete addition
  3. customThe ether layer was separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. washThe combined organic layers were washed with water, 0.1N sulfuric acid
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by flash column chromatography (silica gel, DCM/ethyl acetate, 5:1)
  10. concentrationThe desired fractions were concentrated
  11. customthe residual oil was crystallized from DCM/hexane

출처 및 근거

ORD 기록
ord-6167e100e1f24ccbad6b3eec33a8c4a9
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05274116

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