Sodium Chloride → (4-Chloro-3,5-dimethylpyridin-2-YL)methanol

HRID 2304817ノート

反応式

HRID 2304817 の反応式
[C:1]([C:4]1[C:9]([CH3:10])=[C:8]([Cl:11])[C:7]([CH3:12])=[CH:6][N:5]=1)(O)=[O:2].B.C1COCC1.C1COCC1.O.[Cl-].[Na+]>CN(C)C=O>[Cl:11][C:8]1[C:7]([CH3:12])=[CH:6][N:5]=[C:4]([CH2:1][OH:2])[C:9]=1[CH3:10]

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 2723981Borane;tetrahydrofuranHCID 103134284-Chloro-3,5-dimethylpicolinic AcidHCID 21881883Oxolane--water (1/1)

生成物 1

HCID 9795246(4-Chloro-3,5-dimethylpyridin-2-YL)methanol収率 51%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-carboxy-4-chloro-3,5-lutidine (1 eq.) was suspended in dry dimethylformamide and BH3.THF solution (1M in tetrahydrofuran, 3.5 eq.) was added. The mixture was heated to 60ℑ C. and stirred under a nitrogen atmosphere until completion (1.5 hours). The mixture was cooled in an ice bath and THF/H2O (1:1) mixture (10 volumes) was added slowly. The aqueous layer was saturated with sodium chloride and the tetrahydrofuran layer was separated. The aqueous layer was extracted with ether. The combined organic extracts were dried over sodium sulfate, filtered and the solvent was evaporated under vacuum. The 4-Chloro-2-hydroxymethyl-3,5-Lutidine product was obtained in 51% yield.

後処理

  1. temperatureThe mixture was heated to 60ℑ C
  2. temperatureThe mixture was cooled in an ice bath
  3. customthe tetrahydrofuran layer was separated
  4. extractionThe aqueous layer was extracted with ether
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under vacuum

出典と根拠

ORDレコード
ord-5ec3fd42430845259426df2da796e224
出典データセット
uspto-grants-2002_08
特許番号
US06437139B1

反応ノート

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