Dimethyl Sulfate → Methyl 4-hydroxythiophene-2-carboxylate

HRID 868211노트

반응식

HRID 868211 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=[O:8])[S:5][CH:6]=1.[C:10](=O)(O)[O-].[Na+].COS(OC)(=O)=O>CC(=O)CC>[OH:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1

참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 132779074-Hydroxythiophene-2-carboxylic acid

생성물 1

HCID 13277908Methyl 4-hydroxythiophene-2-carboxylate

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

50.0 g (0.347 mol) of 4-hydroxy-2-thiophenecarboxylic acid and 58.3 g (0.694 mol) of sodium bicarbonate are heated at the boiling point in 900 ml of absolute 2-butanone under nitrogen, and 43.7 g (0.347 mol) of dimethylsulfate are added dropwise in the course of 20 minutes. The mixture is heated under reflux for a further 2.5 hours. It is then evaporated in vacuo and the residue is partitioned between saturated sodium bicarbonate solution and ether. The aqueous phase is extracted five more times with 80 ml of ether each time. The combined organic phases are dried over sodium sulfate/active charcoal, filtered and evaporated.

후처리

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for a further 2.5 hours
  3. customIt is then evaporated in vacuo
  4. customthe residue is partitioned between saturated sodium bicarbonate solution and ether
  5. extractionThe aqueous phase is extracted five more times with 80 ml of ether each time
  6. dry with materialThe combined organic phases are dried over sodium sulfate/active charcoal
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-45a6de1835734273ac33a7171cf215f4
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04778803

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