6-Methyl-5-nitropyridine-2-carbaldehyde → (6-Methyl-5-nitropyridin-2-yl)methanol

HRID 1811589

反応式

HRID 1811589 の反応式
[CH3:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

参加物

4

反応物 2

HCID 30151966-Methyl-5-nitropyridine-2-carbaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 24776197(6-Methyl-5-nitropyridin-2-yl)methanol収率 91%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 6-methyl-5-nitropicolinaldehyde (50 g, 329 mmol) in ethanol (200 mL) was cooled to 10° C. and sodium borohydride (5.9 g, 157 mmol) was added portion-wise. The solution was allowed to stir for one half hour, the ethanol was removed and the residue partitioned between ethyl Acetate and water, the organic phase washed with brine, and dried with magnesium sulfate and stripped. The residue was purified by column chromatography (10-40% ethyl acetate/hexanes) to give (6-methyl-5-nitropyridin-2-yl)methanol (12 g, 91%), a pale white solid. 1HNMR (CDCl3, 400 MHz) δ 2.89 (s, 3H), 3.55 (t, J=5.05, 1H), 4.83 (d, J=4.55, 2H), 7.31 (d, J=8.34, 1H), 8.31 (d, J=8.34, 1H); Exact mass calculated for C7H8N2O3: 168.05. found: 169.10 MS m/z (MH+).

後処理

  1. customthe ethanol was removed
  2. customthe residue partitioned between ethyl Acetate and water
  3. washthe organic phase washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customThe residue was purified by column chromatography (10-40% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-933358bb108e42e68b5a6307b3eae3f8
出典データセット
uspto-grants-2013_01
特許番号
US08362248B2

関連ノート

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