Sodium borohydride → Methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4-(hydroxymethyl)-1-benzothiophen-3-yl)acetate

HRID 591509ノート

反応式

HRID 591509 の反応式
[CH3:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:23]=[C:22]([CH:24]=[O:25])[C:13]3[C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:15][S:16][C:12]=3[CH:11]=2)=[CH:6][CH:5]=[C:4]([CH3:26])[N:3]=1.[BH4-].[Na+]>CO>[CH3:21][O:20][C:18](=[O:19])[CH2:17][C:14]1[C:13]2[C:22]([CH2:24][OH:25])=[CH:23][C:10]([O:9][CH2:8][C:7]3[C:2]([CH3:1])=[N:3][C:4]([CH3:26])=[CH:5][CH:6]=3)=[CH:11][C:12]=2[S:16][CH:15]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 71721633Methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4-formyl-1-benzothiophen-3-yl)acetate

生成物 1

HCID 118667039Methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4-(hydroxymethyl)-1-benzothiophen-3-yl)acetate収率 12.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of methyl 2-(6-((2,6-dimethylpyridin-3-yl)methoxy)-4-formyl-1-benzothiophen-3-yl)acetate (140 mg, 0.38 mmol) in MeOH (3 mL) was added NaBH4 (21.51 mg) at 0° C. After stirring at 0° C. for 1 h, the mixture was quenched with saturated aqueous NH4Cl at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with saturated aqueous NH4Cl and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (17.2 mg).

後処理

  1. customthe mixture was quenched with saturated aqueous NH4Cl at room temperature
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed successively with saturated aqueous NH4Cl and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

出典と根拠

ORDレコード
ord-d6542a03ae534d94acad3627bee37dbf
出典データセット
uspto-grants-2016_01
特許番号
US09238639B2

反応ノート

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