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

HRID 2369487ノート

反応式

HRID 2369487 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-34850f3fb97c450fa70276d371dbf174
出典データセット
uspto-grants-2014_04
特許番号
US08703953B2

反応ノート

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