Methanol → HCID 12112776, compound

HRID 1004167Notes

Reaction equation

HRID 1004167 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].CO.[BH4-].[Na+]>O>[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 887MethanolHCID 4311764Sodium borohydrideHCID 12111908HCID 12111908, compound

Product 1

HCID 12112776HCID 12112776, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 3-acetyl-4-methyl-2,5-di(4-pyridyl)thiophene (200 mg, 0.68 mmol) in MeOH (5 mmol) 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-f3ca1338ebb847f893fdbd12d0878fa4
Source dataset
uspto-grants-2000_04
Patent number
US06048880

Reaction notes

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