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

HRID 2422569ノート

反応式

HRID 2422569 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-bac19b0c6d7140f38ba4ea91741ed8e0
出典データセット
uspto-grants-2011_06
特許番号
US07960409B2

反応ノート

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