Sodium borohydride → 2,2-Difluoro-2-(5-methyl-pyridin-2-yl)-ethanol

HRID 1987046노트

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HRID 1987046 반응식
C([O:3][C:4](=O)[C:5]([F:14])([F:13])[C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][N:7]=1)C.[BH4-].[Na+]>CCO>[F:14][C:5]([F:13])([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][N:7]=1)[CH2:4][OH:3]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 12035972Ethyl Difluoro(5-methylpyridin-2-yl)acetate

생성물 1

HCID 577227102,2-Difluoro-2-(5-methyl-pyridin-2-yl)-ethanol수율 100%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

To a solution of difluoro-(5-methyl-pyridin-2-yl)-acetic acid ethyl ester (10.5 g, 0.05 mol), as prepared in the previous step, in EtOH (98 mL) cooled to 0° C. was added NaBH4 (3.7 g, 0.098 mol, 2×). After 3 h the reaction was carefully quenched with saturated NH4Cl (100 mL) and partitioned with EtOAc (200 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo to afford the product as a white solid (8.5 g, 0.05 mol, 100% crude yield). 1H NMR (300 Hz, CDCl3) δ 8.43 (s, 1H), 7.66 (m, 2H), 4.22 (t, J=12.3 Hz), 2.41 (s, 1H); LC/MS (m/z) [M+1]+ 174.1 (calculated for C8H10F2NO, 174.2).

후처리

  1. customAfter 3 h the reaction was carefully quenched with saturated NH4Cl (100 mL)
  2. custompartitioned with EtOAc (200 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9bbc14616ef543899f0b56f1d025c39e
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550474B2

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