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

HRID 2304817노트

반응식

HRID 2304817 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5ec3fd42430845259426df2da796e224
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06437139B1

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