Carbon Dioxide → 2-Methyl-3-Hydroxy-4-Hydroxymethyl-5-Fluoromethyl-Pyridine

HRID 839525

반응식

HRID 839525 반응식
S(F)(F)(F)[F:2].[CH2-]C(C)=O.[CH3:10][C:11]1[C:16]([OH:17])=[C:15]([CH2:18][OH:19])[C:14]([CH2:20]O)=[CH:13][N:12]=1.C(=O)=O.CC(C)=O.C(=O)=O.Cl>>[CH3:10][C:11]1[C:16]([OH:17])=[C:15]([CH2:18][OH:19])[C:14]([CH2:20][F:2])=[CH:13][N:12]=1

참가 물질

7

반응물 6

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 1054PyridoxineHCID 24555Sulfur tetrafluorideHCID 18522661Acetone cardiceHCID 178477758HCID 178477758, 화합물

생성물 1

HCID 125108182-Methyl-3-Hydroxy-4-Hydroxymethyl-5-Fluoromethyl-Pyridine

실험 절차

Sulfur tetrafluoride (41 mg.-mole) is passed into 40 ml. of liquid HF, cooled in a dry-ice-acetone bath, then, acetonide of 2-methyl-3-hydroxy-4-hydroxymethyl-5-hydroxymethyl pyridine, (4.18 g.; 20 mg.-mole) is added under continuing cooling. The dry-ice-acetone bath is not replenished with dry-ice and the mixture is left standing in it overnight. After blowing off the remaining HF at room temperature, conc. aq. HCl is added, evaporated to dryness in vacuo, the residue is redissolved in 20 ml. of 1M aq. HCl, heated on the steam-bath for 15 minutes, (for hydrolysis of the acetonide, charcoaled and evaporated to dryness, redissolved in water, then passed through a Dowex 50 × 2 cation-exchange resin column, washed free of F⃝ with water.

후처리

  1. temperatureof liquid HF, cooled in a dry-ice-acetone bath
  2. temperatureunder continuing cooling
  3. waitthe mixture is left
  4. customstanding in it overnight
  5. customat room temperature
  6. customevaporated to dryness in vacuo
  7. dissolutionthe residue is redissolved in 20 ml
  8. temperatureof 1M aq. HCl, heated on the steam-bath for 15 minutes
  9. custom(for hydrolysis of the acetonide
  10. customevaporated to dryness
  11. dissolutionredissolved in water
  12. washwashed free of F⃝ with water

출처 및 근거

ORD 기록
ord-123d7525db764acab27efe24f1d2c49f
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04096180

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