Solketal → 3-[(3-Methoxypyridin-2-yl)oxy]propane-1,2-diol

HRID 444444

반응식

HRID 444444 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[C:6]([N+]([O-])=O)=[N:7][CH:8]=[CH:9][CH:10]=1.CC1(C)[O:19][CH2:18][CH:17]([CH2:20][OH:21])[O:16]1>CN(C)P(=O)(N(C)C)N(C)C>[CH3:3][O:4][C:5]1[C:6]([O:19][CH2:18][CH:17]([OH:16])[CH2:20][OH:21])=[N:7][CH:8]=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 7528SolketalHCID 24758Sodium hydrideHCID 5560633-Methoxy-2-nitropyridine

생성물 1

HCID 131950743-[(3-Methoxypyridin-2-yl)oxy]propane-1,2-diol

시약·촉매·용매 1

HCID 12679Hexamethylphosphoramide용매

실험 절차

26.5 g of sodium hydride are added in the course of one hour to a mixture of 161 g of 3-methoxy-2-nitropyridine and 144 g of 2,2-dimethyl-5-hydroxymethyl-1,3-dioxolane in 1,000 ml of hexamethylphosphoric acid triamide, with stirring; by means of cooling, the temperature is kept at 0°-10° during the addition. The reaction mixture is then stirred for a further 5 hours with ice-cooling and then for 15 hours at room temperature. The reaction mixture is poured onto ice and extracted with diethyl ether. The organic extract is washed with a concentrated aqueous solution of sodium chloride, dried and evaporated. The residue is dissolved in 1,000 ml of ethanol, 100 ml of 2 N hydrochloric acid are added and the mixture is left to stand for 8 hours. After evaporating off the solvent, the residue is rendered alkaline with a concentrated solution of sodium hydroxide in water and extracted with ethyl acetate. Evaporating off the solvent yields a crude product from which crystalline 3-(3-methoxy-2-pyridyloxy)-1,2-propanediol with a melting point of 62°-65° is obtained on the addition of diethyl ether.

후처리

  1. temperatureby means of cooling
  2. additionthe temperature is kept at 0°-10° during the addition
  3. stirringThe reaction mixture is then stirred for a further 5 hours with ice-
  4. temperaturecooling
  5. additionThe reaction mixture is poured onto ice
  6. extractionextracted with diethyl ether
  7. extractionThe organic extract
  8. washis washed with a concentrated aqueous solution of sodium chloride
  9. customdried
  10. customevaporated
  11. dissolutionThe residue is dissolved in 1,000 ml of ethanol
  12. addition100 ml of 2 N hydrochloric acid are added
  13. waitthe mixture is left
  14. waitto stand for 8 hours
  15. customAfter evaporating off the solvent
  16. extractionextracted with ethyl acetate
  17. customEvaporating off the solvent

출처 및 근거

ORD 기록
ord-cb9ffa13d32d4036b5c5f24a2f2a61e9
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04264599

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