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

HRID 1811589

반응식

HRID 1811589 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-933358bb108e42e68b5a6307b3eae3f8
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362248B2

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