Sodium hydride → HCID 19874529, compound

HRID 465461Notes

Reaction equation

HRID 465461 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1.[N+]([C:17]1[O:21][C:20]([C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:18]=1)([O-])=O>CS(C)=O>[CH2:10]([C:7]1[CH:6]=[CH:5][C:4]([O:3][C:17]2[O:21][C:20]([C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:18]=2)=[CH:9][CH:8]=1)[C:11]([CH3:12])=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 94882Methyl 5-nitro-2-furoateHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 19874529HCID 19874529, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (1.1 g of an 80% dispersion in oil) was added, with vigorous stirring to a solution of (4-hydroxyphenyl)propan-2-one, ethylene ketal (6.8 g) in dimethylsulphoxide (50 ml). After 30 minutes, methyl 5 nitrofuran-2-carboxylate (5 g) was added and the resulting mixture was stirred and heated at 80°-90° C. for 10 hr. The cooled reaction mixture was poured into ice-water and extracted into diethylether. The organic layer was washed with 5% potassium hydroxide solution and water, dried (MgSO4) and evaporated to an oil which was chromatographed on silica gel. Elution with chloroform gave methyl 5-[4-acetonylphenoxy]-furan-2-carboxylate, ethylene ketal (3.3 g) which was taken up in a 1:1 mixture of methanol and 2N hydrochloric acid and stirred at ambient temperature for 4 hr. Evaporation of the methanol and extraction of the aqueous residue into dichloromethane gave an oil which was chromatographed on silica gel. Elution with chloroform gave methyl 5-[4-acetonylphenoxy]furan-2-carboxylate.

Workup

  1. temperatureheated at 80°-90° C. for 10 hr
  2. customThe cooled reaction mixture
  3. extractionextracted into diethylether
  4. washThe organic layer was washed with 5% potassium hydroxide solution and water
  5. dry with materialdried (MgSO4)
  6. customevaporated to an oil which
  7. customwas chromatographed on silica gel
  8. washElution with chloroform

Sources & evidence

ORD record
ord-30cd02c603944cc0b10d3ec4a4946b26
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

Loading…