Ethyl formate → HCID 22666483, compound

HRID 1007920Notes

Reaction equation

HRID 1007920 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:20])[CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([OH:19])=[C:14]([C:16](=[O:18])[CH3:17])[CH:15]=1.[CH:21](OCC)=O.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:20][N:4]([CH3:3])[CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]1[CH:15]=[C:14]2[C:13](=[CH:12][CH:11]=1)[O:19][CH:21]=[CH:17][C:16]2=[O:18]

Participants

7

Reactant 4

HCID 8025Ethyl formateHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 22666328HCID 22666328, compound

Product 1

HCID 22666483HCID 22666483, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In 3.0 mL of toluene is suspended 0.44 g of sodium hydride (60% mineral oil suspension), to which is dropwise added, at an ice-cooled temperature, a mixture of 0.93 g of 1-(5-{2-[2-(dimethylamino)ethoxy]-ethyl}-2-hydroxyphenyl)-1-ethanone, 6.0 mL of toluene and 9.0 mL of ethyl formate. The resulting mixture is stirred at ambient temperature for one hour. Ice water and ethyl acetate are added to the reaction mixture, pH is adjusted to 11 with anhydrous potassium carbonate, and the organic layer is separated. The aqueous layer is twice extracted with ethyl acetate, and then the aqueous layer is salted out and further extracted once with ethyl acetate and four times with chloroform. The organic layers are collected and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is dissolved in 13 mL of acetic acid, 6.5 mL of 12 mol/L aqueous hydrochloric acid is added, and the resulting mixture is stirred at 60° C. for 15 minutes. After cooling, chloroform and water are added, pH is adjusted to 7.0 with anhydrous potassium carbonate, and the organic layer is separated. The organic layer is dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: chloroform:methanol=50:1 to 5:1) to obtain 6-{2-[2-(dimethylamino)ethoxy]-ethyl}-4H-chromen-4-one as an oily product.

Workup

  1. temperaturecooled temperature
  2. customthe organic layer is separated
  3. extractionThe aqueous layer is twice extracted with ethyl acetate
  4. extractionfurther extracted once with ethyl acetate and four times with chloroform
  5. customThe organic layers are collected
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. dissolutionThe residue is dissolved in 13 mL of acetic acid
  9. addition6.5 mL of 12 mol/L aqueous hydrochloric acid is added
  10. stirringthe resulting mixture is stirred at 60° C. for 15 minutes
  11. temperatureAfter cooling
  12. additionchloroform and water are added
  13. customthe organic layer is separated
  14. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  15. distillationthe solvent is distilled off under reduced pressure
  16. customthe residue is purified by column chromatography (eluent: chloroform:methanol=50:1 to 5:1)

Sources & evidence

ORD record
ord-01b267a821154c6d9ecdc3bff3aa6691
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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