Tetrahydrofuran → HCID 19759370, compound

HRID 248386Notes

Reaction equation

HRID 248386 reaction equation
[Si](OC[C:20]1([C:36]#[N:37])[CH2:24][CH:23]=[CH:22][N:21]1[C:25]1[CH:30]=[CH:29][C:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:27][CH:26]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:56]1CCC[CH2:57]1>>[CH2:34]([O:33][C:31]([C:28]1[CH:27]=[CH:26][C:25]([N:21]2[C:22]([CH2:57][OH:56])=[CH:23][CH:24]=[C:20]2[C:36]#[N:37])=[CH:30][CH:29]=1)=[O:32])[CH3:35]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 131717903HCID 131717903, compound

Product 1

HCID 19759370HCID 19759370, compound

Procedure

To a solution of 2-tert-butyldiphenylsilyloxymethyl-1-(4-ethoxycarbonylphenyl)pyrrole-2-carbonitrile (1.9 g) in tetrahydrofuran (19 ml) was added tetrabutylammonium fluoride (5.6 ml, 1M tetrahydrofuran solution) through syringe at ambient temperature. The mixture was stirred for half an hour at the same temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate and the solution was washed with aqueous hydrochloric acid, water and brine, and then dried, and concentrated in vacuo. The oily residue was chromatographed on silica gel (elution by ethyl acetate/n-hexane=1/1) to give 1-(4-ethoxycarbonylphenyl)-5-hydroxymethylpyrrole-2-carbonitrile (702.5 mg) as an oil.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed with aqueous hydrochloric acid, water and brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was chromatographed on silica gel (elution by ethyl acetate/n-hexane=1/1)

Sources & evidence

ORD record
ord-8dff85372ba648a886799ae994b26618
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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