Acetone → HCID 13136947, compound

HRID 851210Notes

Reaction equation

HRID 851210 reaction equation
Br.[OH:2][C:3]1[C:8]([OH:9])=[CH:7][C:6]2[C:10]3[CH2:15][CH2:14][N:13]([CH2:16][C:17](=[O:19])[CH3:18])[CH2:12][C:11]=3[C:20](=[O:22])[O:21][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:33][CH3:34])(=O)=O.[CH3:38][C:39](C)=O>>[CH2:33]([O:2][C:3]1[C:8]([O:9][CH2:38][CH3:39])=[CH:7][C:6]2[C:10]3[CH2:15][CH2:14][N:13]([CH2:16][C:17](=[O:19])[CH3:18])[CH2:12][C:11]=3[C:20](=[O:22])[O:21][C:5]=2[CH:4]=1)[CH3:34]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6163Diethyl Sulfate2×HCID 11430Potassium CarbonateHCID 20502576HCID 20502576, compound

Product 1

HCID 13136947HCID 13136947, compound

Procedure

A mixture of 1,2,3,4-tetrahydro-8,9-dihydroxy-3-(2-oxopropyl)-5H-[1]benzopyrano[3,4-c]pyridin-5-one hydrobromide (108 g, 0.29 moles), potassium carbonate (155 g, 1.12 moles), and diethyl sulfate (118 g, 0.76 moles) in 2.5 l of acetone is stirred at reflux for 21 hours. Additional diethyl sulfate (59 g, 0.38 moles) is added, and the mixture is heated for an additional 30 hours. The cooled mixture is filtered, and the filter cake is digested twice in hot acetone (500 ml) and refiltered. The combined filtrates are evaporated, and the residue is distributed between dichloromethane (1500 ml) and water (750 ml). The organic layer is separated, washed 4 times with 2.5% aqueous sodium hydroxide (750 ml), dried over sodium sulfate, and evaporated. The residue is recrystallized as the free base from methanol and washed with cold hexane to yield the final product (36.3 g), mp 146°-148° C.

Workup

  1. temperatureat reflux for 21 hours
  2. temperaturethe mixture is heated for an additional 30 hours
  3. filtrationThe cooled mixture is filtered
  4. customThe combined filtrates are evaporated
  5. customThe organic layer is separated
  6. washwashed 4 times with 2.5% aqueous sodium hydroxide (750 ml)
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue is recrystallized as the free base from methanol
  10. washwashed with cold hexane

Sources & evidence

ORD record
ord-b600026516864cc7966f04f1d6bcd469
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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