Water → HCID 12112776, compound

HRID 2121713Notes

Reaction equation

HRID 2121713 reaction equation
[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[S:6][C:5]=1[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O>CO>[N:19]1[CH:20]=[CH:21][C:16]([C:5]2[S:6][C:7]([C:10]3[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=3)=[C:8]([CH3:9])[C:4]=2[CH:1]([OH:3])[CH3:2])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 12111908HCID 12111908, compound

Product 1

HCID 12112776HCID 12112776, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-acetyl-4-methyl-2,5-di(4-pyridyl)thiophene (200 mg, 0.68 mmol) in MeOH (5 mL) was added sodium borohydride (30 mg, 0.79 mmol) at 0° C., and the mixture was stirred for 2 hours. Water (5 mL) was added to the mixture. The whole was extracted with ethyl acetate (50 mL), the organic layer washed with brine, dried over MgSO4, and concentrated in vacuo. The resulting residue was purified by flash chromatography eluting with CH2Cl2-MeOH (20:1) to provide the title product as a solid. Recrystallized from ethyl acetate gave the title product (130 mg, 75% yield).

Workup

  1. extractionThe whole was extracted with ethyl acetate (50 mL)
  2. washthe organic layer washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography
  6. washeluting with CH2Cl2-MeOH (20:1)

Sources & evidence

ORD record
ord-1d4e3ec339474570accca68cca47b8c0
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

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