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

HRID 2369487노트

반응식

HRID 2369487 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

반응 조건

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-34850f3fb97c450fa70276d371dbf174
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703953B2

반응 노트

불러오는 중…