硼氢化钠 → 2-Pyridinemethanol, 6-[(difluoromethoxy)methyl]-

HRID 876986

反应方程式

HRID 876986 反应方程式
[BH4-].[Na+].[F:3][CH:4]([F:18])[O:5][CH2:6][C:7]1[N:12]=[C:11]([C:13](OCC)=[O:14])[CH:10]=[CH:9][CH:8]=1>CCO>[F:18][CH:4]([F:3])[O:5][CH2:6][C:7]1[N:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][CH:8]=1

参与物

4

反应物 2

HCID 4311764硼氢化钠HCID 66718372Ethyl 6-difluoromethoxymethylpyridine-2-carboxylate

产物 1

HCID 667184182-Pyridinemethanol, 6-[(difluoromethoxy)methyl]-收率 80%

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

反应条件

温度
80 °C

实验过程

NaBH4 (377 mg, 9.96 mmol) was added to a solution of ethyl 6-difluoromethoxymethylpyridine-2-carboxylate (2.30 g, 9.96 mmol) in EtOH (50 mL) at 0° C., the mixture was warmed to 80° C. and stirred for 5 h. The mixture was cooled to 0° C., quenched with sat. aq. NH4Cl, concentrated in vacuo and partitioned between EtOAc and brine. The organic layer was separated, dried (MgSO4), filtered and evaporated to give the title compound (1.50 g, 80%) as a colorless oil; NMR δH (400 MHz, CDCl3) 7.73 (1H, t, J 8.0 Hz), 7.35 (1H, d, J 8.0 Hz), 7.19 (1H, d, J 8.0 Hz), 6.39 (1H, t, J 74.0 Hz), 5.02 (2H, s), 4.76 (2H, s); (M+H)+ 190.

后处理

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched with sat. aq. NH4Cl
  3. concentrationconcentrated in vacuo
  4. custompartitioned between EtOAc and brine
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

来源与证据

ORD记录
ord-6cd9753ac33f4a8a962a097181733aaf
来源数据集
uspto-grants-2015_03
专利号
US08987279B2

关联笔记

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