Sodium borohydride → (4-(4-Chloro-2-fluorophenyl)pyridin-3-yl)methanol

HRID 870897ノート

反応式

HRID 870897 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=[O:15])=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:4]([F:16])[CH:3]=1.[BH4-].[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][N:11]=[CH:12][C:13]=2[CH2:14][OH:15])=[C:4]([F:16])[CH:3]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 866958904-(4-Chloro-2-fluorophenyl)nicotinaldehyde

生成物 1

HCID 86695891(4-(4-Chloro-2-fluorophenyl)pyridin-3-yl)methanol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-(4-chloro-2-fluorophenyl)nicotinaldehyde (3 g, 12.73 mmol) in a mixture of methanol (5 mL) and tetrahydrofuran (5 mL) cooled to 0° C. was added NaBH4 (0.722 g, 19.10 mmol) and the solution stirred for 30 min. The reaction was quenched by addition of water (10 mL). The solution was extracted with ethyl acetate (3×15 mL). The combined organic extracts were washed with water (1×15 mL) and brine (1×15 mL), dried with sodium sulfate and concentrated under reduced pressure to yield (4-(4-chloro-2-fluorophenyl)pyridin-3-yl)methanol that was used without further purification in the next step. LCMS (ESI) m/e 238 [(M+H)+, calcd for C12H10ClFNO 238.0].

後処理

  1. customThe reaction was quenched by addition of water (10 mL)
  2. extractionThe solution was extracted with ethyl acetate (3×15 mL)
  3. washThe combined organic extracts were washed with water (1×15 mL) and brine (1×15 mL)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-56d0ed09e7074d2aa6823c23cf2a9d9f
出典データセット
uspto-grants-2015_03
特許番号
US08969564B2

反応ノート

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