Ethanol → HCID 19874553, compound

HRID 465466Notes

Reaction equation

HRID 465466 reaction equation
[CH3:1][NH2:2].[CH2:3]([C:7]1[CH:23]=[CH:22][C:10]([O:11][CH2:12][CH:13]2[O:17][CH:16]([C:18](OC)=O)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)[C:4]([CH3:6])=[O:5].C([OH:26])C>>[CH3:18][C:16]1([C:1]([NH2:2])=[O:26])[CH2:15][CH2:14][CH:13]([CH2:12][O:11][C:10]2[CH:22]=[CH:23][C:7]([CH2:3][C:4]([CH3:6])=[O:5])=[CH:8][CH:9]=2)[O:17]1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 6329MethylamineHCID 19874542HCID 19874542, compound

Product 1

HCID 19874553HCID 19874553, compound

Procedure

Methylamine (15 ml of a 33% solution in ethanol) was added, dropwise, to a stirred solution of methyl 5-[4-acetonylphenoxymethyl]tetrahydrofuran-2-carboxylate, ethylene ketal (4.1 g) in ethanol (80 ml). The reaction mixture was stirred and heated under reflux for 4 hr, cooled and evaporated to an oil which was dissolved in a mixture of methanol (40 ml) and 2N hydrochloric acid (40 ml) and stirred at ambient temperature for 3 hr. The methanol was evaporated and the aqueous residue was extracted into dichloromethane. The organic extract was dried (MgSO4) and evaporated to an oil which was purified by column chromatography on silica gel. Elution with methanol in chloroform (2:98) gave methyl 5-[4-acetonylphenoxymethyl]tetrahydrofuran-2-carboxamide.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hr
  3. temperaturecooled
  4. customevaporated to an oil which
  5. dissolutionwas dissolved in a mixture of methanol (40 ml) and 2N hydrochloric acid (40 ml)
  6. stirringstirred at ambient temperature for 3 hr
  7. customThe methanol was evaporated
  8. extractionthe aqueous residue was extracted into dichloromethane
  9. extractionThe organic extract
  10. dry with materialwas dried (MgSO4)
  11. customevaporated to an oil which
  12. customwas purified by column chromatography on silica gel
  13. washElution with methanol in chloroform (2:98)

Sources & evidence

ORD record
ord-4f8a6fcf09284b459c809e9f55af0c44
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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