Sodium borohydride → 2-Pyridinemethanol, 6-[(difluoromethoxy)methyl]-

HRID 2207567

反応式

HRID 2207567 の反応式
[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

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 66718372Ethyl 6-difluoromethoxymethylpyridine-2-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7f3e90bb013f4afda2e16b5db8d072c3
出典データセット
uspto-grants-2016_06
特許番号
US09376443B2

関連ノート

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