Sodium borohydride → 6-Butoxy-2-hydroxymethylpyridine

HRID 912699노트

반응식

HRID 912699 반응식
[CH2:1]([O:5][C:6]1[N:11]=[C:10]([C:12](OC)=[O:13])[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>C(O)C>[CH2:1]([O:5][C:6]1[N:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydride3회HCID 67415067Methyl 6-butoxypyridine-2-carboxylate

생성물 1

HCID 197561166-Butoxy-2-hydroxymethylpyridine수율 91%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Methyl 6-butoxypyridine-2-carboxylate (2.46 g, 11.8 mmol, obtained from Example 17(b)) was dissolved in absolute ethanol (112 mL) and sodium borohydride (1.78 g, 47.0 mmol, 4 equiv.) was added. After refluxing for 1 h, another 2 equivalents of sodium borohydride were added and then after 2 h more an additional 2 equivalents more sodium borohydride were added. After another 3 h the reaction was cooled to r.t. and concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo producing 1.92 g (91% yield, 10.7 mmol) of the title compound as a clear liquid.

후처리

  1. temperatureAfter refluxing for 1 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between water and ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-521de58ff919405e8aedb28e2ae56921
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026244B2

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