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

HRID 591509노트

반응식

HRID 591509 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d6542a03ae534d94acad3627bee37dbf
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238639B2

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