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

HRID 839525

反応式

HRID 839525 の反応式
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

参加物

7

反応物 6

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 1054PyridoxineHCID 24555Sulfur tetrafluorideHCID 18522661Acetone cardiceHCID 178477758HCID 178477758、化合物

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-123d7525db764acab27efe24f1d2c49f
出典データセット
uspto-grants-1978_06
特許番号
US04096180

関連ノート

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