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

HRID 870897노트

반응식

HRID 870897 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-56d0ed09e7074d2aa6823c23cf2a9d9f
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969564B2

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