Sodium borohydride → (5-Chloro-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanol

HRID 2074518ノート

反応式

HRID 2074518 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH:22]=[O:23])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])=[N:7]2.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH2:22][OH:23])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:20])([F:21])[F:19])=[N:7]2

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 575561835-Chloro-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde

生成物 1

HCID 67090613(5-Chloro-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 5-chloro-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde (2.1673 g, 6.456 mmol) in 32 mL of THF at 0° C. was added sodium borohydride (0.3664 g, 9.684 mmol) and the mixture was stirred at 0° C. After 1 hr at 0° C., the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL), and the organic layer was washed with brine (50 mL×3), dried over Na2SO4, filtered, and concentrated under reduced pressure to give (5-chloro-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanol as a yellow syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.68-8.73 (1 H, m), 7.96-8.02 (1 H, m), 7.90-7.95 (1 H, m), 7.83-7.87 (1 H, m), 7.68-7.83 (3 H, m), 7.50-7.58 (1 H, m), 5.63 (1 H, t, J=5.3 Hz), 4.36 (2 H, br. s.); LC-MS (ESI) m/z 338.0 [M+H]+. The product was carried on crude without purification for the next step.

後処理

  1. customthe mixture was partitioned between EtOAc (100 mL) and H2O (100 mL)
  2. washthe organic layer was washed with brine (50 mL×3)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-20b9747a3e4b47ae81d1a6a1d3a25aa9
出典データセット
uspto-grants-2011_04
特許番号
US07919498B2

反応ノート

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