Sodium borohydride → HCID 67115789、化合物

HRID 72573ノート

反応式

HRID 72573 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:25])=[C:6]([CH:24]=1)[CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][N:13](C(=O)C(F)(F)F)[C:12]=2[CH:23]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:25])=[C:6]([CH:24]=1)[CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][NH:13][C:12]=2[CH:23]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 583408561-[6-(5-Bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

生成物 1

HCID 67115789HCID 67115789、化合物収率 91%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirred solution of 1-[6-(5-bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (8.6 g, 19.8 mmol) in ethanol (40 mL) was added NaBH4 (1.5 g, 39.0 mmol) portion wise and the reaction mixture was stirred overnight. Excess of NaBH4 was quenched by adding aq. NH4Cl, and ethanol was evaporated. The residue was partitioned between ethyl acetate and water, and the organic layer was separated, washed with brine (40 mL) and dried over sodium sulphate. Crude product obtained after evaporation of solvent was purified by silica gel column chromatography to furnish 6-(5-bromo-2-chloro-benzyl)-3,4-dihydro-2H-benzo[1,4]oxazine (6.1 g).

後処理

  1. customExcess of NaBH4 was quenched
  2. additionby adding aq. NH4Cl, and ethanol
  3. customwas evaporated
  4. customThe residue was partitioned between ethyl acetate and water
  5. customthe organic layer was separated
  6. washwashed with brine (40 mL)
  7. dry with materialdried over sodium sulphate
  8. customCrude product obtained
  9. customafter evaporation of solvent
  10. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-27b0ff796a2f4763b30295d720fd1d9c
出典データセット
uspto-grants-2014_09
特許番号
US08828951B2

反応ノート

読み込み中…