Water → HCID 18470714, compound

HRID 2228625Notes

Reaction equation

HRID 2228625 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)[NH:6][C:5]=1[CH:16]=[O:17])(=[O:3])[CH3:2].[BH4-].[Na+].O>C(Cl)Cl.CO>[C:1]([C:4]1[C:8]([CH3:9])=[C:7]([C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)[NH:6][C:5]=1[CH2:16][OH:17])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 18470693HCID 18470693, compound

Product 1

HCID 18470714HCID 18470714, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-acetyl-2-formyl-4-methyl-5-(4-pyridyl)-1H-pyrrole (84 mg, 0.37 mmol) in CH2Cl2 (2 mL) and methanol (2 mL) was added sodium borohydride (14 mg, 0.37 mmol) at 0° C. and stirred for 30 minutes at room temperature. The mixture was poured into water (15 mL) and extracted with ethyl acetate-ethanol (10:1, 20 mL×3). The combined organic layers were washed with brine, dried over MgSO4, and evaporated in vactio. Recrystallization from ethyl acetate provided the title compound (20 mg, 24% yield) as a solid.

Workup

  1. extractionextracted with ethyl acetate-ethanol (10:1, 20 mL×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vactio
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-505a0dbecf4749f189f27fef651b163b
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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