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

HRID 591509Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-d6542a03ae534d94acad3627bee37dbf
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238639B2

Reaction notes

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