Sodium borohydride → 6-Butoxy-2-hydroxymethylpyridine

HRID 912699ノート

反応式

HRID 912699 の反応式
[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]

参加物

4

反応物 2

HCID 4311764Sodium borohydride3 回HCID 67415067Methyl 6-butoxypyridine-2-carboxylate

生成物 1

HCID 197561166-Butoxy-2-hydroxymethylpyridine収率 91%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-521de58ff919405e8aedb28e2ae56921
出典データセット
uspto-grants-2011_09
特許番号
US08026244B2

反応ノート

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