Sodium borohydride → 7-(2-Hydroxyethyl)-4-phenylquinoline-2-carbonitrile

HRID 2422569노트

반응식

HRID 2422569 반응식
[O:1]=[CH:2][CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:9][C:10]([C:14]#[N:15])=[N:11]2)=[CH:6][CH:5]=1.[BH4-].[Na+]>C1COCC1.CO>[OH:1][CH2:2][CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:9][C:10]([C:14]#[N:15])=[N:11]2)=[CH:6][CH:5]=1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 597749037-(2-Oxoethyl)-4-phenylquinoline-2-carbonitrile

생성물 1

HCID 597748837-(2-Hydroxyethyl)-4-phenylquinoline-2-carbonitrile

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 7-(2-oxoethyl)-4-phenylquinoline-2-carbonitrile (1.5 g, 5.5 mmol) in THF (30 mL) and MeOH (10 mL) was added portionwise at 0° C. sodium borohydride (320 mg, 8.4 mmol). The mixture was stirred overnight at rt. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 concentrated under reduced pressure and purified on silica gel (eluting with ethyl acetate/hexanes, 1:1) to give the title compound. MS (+ESI): 275 (M+H)+.

후처리

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified on silica gel (eluting with ethyl acetate/hexanes, 1:1)

출처 및 근거

ORD 기록
ord-bac19b0c6d7140f38ba4ea91741ed8e0
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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