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

HRID 1987046ノート

反応式

HRID 1987046 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9bbc14616ef543899f0b56f1d025c39e
出典データセット
uspto-grants-2009_06
特許番号
US07550474B2

反応ノート

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