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

HRID 2096690

反应方程式

HRID 2096690 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-02f4d9f73b244ea28b71efe08d032652
来源数据集
uspto-grants-2013_05
专利号
US08450328B2

关联笔记

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