Water → 3-Benzoylpyrrole

HRID 327843

Reaction equation

HRID 327843 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 27732343-Benzoylpyrrole

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent3×

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-6167e100e1f24ccbad6b3eec33a8c4a9
Source dataset
uspto-grants-1993_12
Patent number
US05274116

Linked notes

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