Tetrahydrofuran → [1-(1-Hydroxypropan-2-yl)-2,5-dimethyl-1H-pyrrol-3-yl](phenyl)methanone

HRID 224657Notes

Reaction equation

HRID 224657 reaction equation
C([O:4][CH2:5][CH:6]([N:8]1[C:12]([CH3:13])=[CH:11][C:10]([C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]1[CH3:22])[CH3:7])(=O)C.O1CCCC1.[OH-].[Na+]>CO>[C:14]([C:10]1[CH:11]=[C:12]([CH3:13])[N:8]([CH:6]([CH3:7])[CH2:5][OH:4])[C:9]=1[CH3:22])(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 12603260HCID 12603260, compound

Product 1

HCID 194460[1-(1-Hydroxypropan-2-yl)-2,5-dimethyl-1H-pyrrol-3-yl](phenyl)methanoneYield 74.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 10 ml of methanol was dissolved 1.24 g (4.15 mmoles) of 2-(3-benzoyl-2,5-dimethylpyrrol-1-yl)-2-methylethyl acetate. Tetrahydrofuran (30 ml) and then 10 ml (10.0 mmoles) of an 1.0 N aqueous solution of sodium hydroxide was added. The mixture was stirred for 3 hours at room temperature. The solvent was distilled off under reduced pressure. The residue was extracted with 50 ml of ethyl acetate three times, and the resulting extracts were dried over anhydrous magnesium sulfate, and concentrated to afford 900 mg of a crude product. The crude product was chromatographed on a column of silica gel using cyclohexane/ethyl acetate (1/1) as an eluent to afford compound (106) (790 mg, 3.07 mmoles, 74.1%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionThe residue was extracted with 50 ml of ethyl acetate three times
  3. dry with materialthe resulting extracts were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto afford 900 mg of a crude product
  6. customThe crude product was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-47460e2fec2b4843a6e3f8c4697e7bd0
Source dataset
uspto-grants-1980_11
Patent number
US04233309

Reaction notes

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