Sodium borohydride → HCID 86680634, compound

HRID 1497475Notes

Reaction equation

HRID 1497475 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]2[CH:10]=[CH:11][C:12](=[O:16])[N:13]([CH3:15])[CH:14]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C1COCC1.CO>[OH:3][CH:1]([C:4]1[S:8][C:7]([C:9]2[CH:10]=[CH:11][C:12](=[O:16])[N:13]([CH3:15])[CH:14]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86680487HCID 86680487, compound

Product 1

HCID 86680634HCID 86680634, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(5-acetylthiophen-2-yl)-1-methylpyridin-2(1H)-one (0.65 g, 2.78 mmol) in THF (8 mL) and MeOH (8 mL) was added NaBH4 (0.26 g, 6.97 mmol) under nitrogen. The mixture was stirred at rt for 10 min, quenched with ammonium chloride solution (15 mL) and extracted with ethyl acetate (2×100 mL). The organic extracts were washed with brine solution (2×50 mL), dried over sodium sulphate and evaporated to obtain the crude compound. Purification by flash chromatography (100-200μ; 100% ethyl acetate) afforded 5-(5-(1-hydroxyethyl)thiophen-2-yl)-1-methylpyridin-2(1H)-one (0.5 g, 76% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.00 (s, 1H), 7.69 (d, 1H), 7.07 (d, 1H), 6.83 (d, 1H), 6.43 (d, 1H), 5.51 (bs, 1H), 4.88 (q, 1H), 3.45 (s, 3H), 1.38 (d, 3H); LC-MS m/z calcd for [M+H]+ 236.07 found 236.3.

Workup

  1. customquenched with ammonium chloride solution (15 mL)
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe organic extracts were washed with brine solution (2×50 mL)
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto obtain the crude compound
  7. customPurification by flash chromatography (100-200μ; 100% ethyl acetate)

Sources & evidence

ORD record
ord-0b4c7791b94f4c1cb4e57b5ebea0ee5f
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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