Methanol → (3,4-Dichloropyridin-2-yl)methanol

HRID 1655207ノート

反応式

HRID 1655207 の反応式
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:14]([CH3:20])=[N:15][CH:16]=[CH:17][C:18]=1[Cl:19].FC(F)(F)C(OC(=O)C(F)(F)F)=O.CO>ClCCl>[Cl:12][C:13]1[C:14]([CH2:20][OH:9])=[N:15][CH:16]=[CH:17][C:18]=1[Cl:19]

参加物

6

反応物 4

HCID 887MethanolHCID 9845Trifluoroacetic anhydrideHCID 70297m-Chloroperbenzoic acidHCID 219228903,4-Dichloro-2-methylpyridine

生成物 1

HCID 22117301(3,4-Dichloropyridin-2-yl)methanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

m-Chloroperbenzoic acid (32.63 g) in dichloromethane (400 ml) was added dropwise to a solution of 3,4 -dichloro-2 -picoline (25.53 g)in dichloromethane (100 ml) maintaining the temperature at 20°-25°. After standing for 16 hours at room temperature the solution was washed with 1 N NAOH, dried (K2CO3 ) and filtered to give a pale yellow solution. Trifluoroacetic anhydride (30 ml) was added dropwise to this solution maintaining the temperature at 15°-20°. After standing for 2 days at room temperature, methanol (100 ml) was added and the solution evaporated under reduced presure. The residue was treated with aqueous sodium carbonate and extracted into dichloromethane. After drying (K2CO3 ) and removal of solvent, the residue was recrystallised from pet. ether (60/80 ) to give 3,4 -dichloro-2 -hydroxymethylpyridine, 15.76 g, m.p. 66°-8°.

後処理

  1. temperaturemaintaining the temperature at 20°-25°
  2. washthe solution was washed with 1 N NAOH
  3. dry with materialdried (K2CO3 )
  4. filtrationfiltered
  5. customto give a pale yellow solution
  6. temperaturemaintaining the temperature at 15°-20°
  7. waitAfter standing for 2 days at room temperature
  8. customthe solution evaporated under reduced presure
  9. additionThe residue was treated with aqueous sodium carbonate
  10. extractionextracted into dichloromethane
  11. customAfter drying
  12. custom(K2CO3 ) and removal of solvent
  13. customthe residue was recrystallised from pet. ether (60/80 )

出典と根拠

ORDレコード
ord-080221254b7f41feb105af8a698e71e2
出典データセット
uspto-grants-1993_10
特許番号
US05250527

反応ノート

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