Tetrabutylammonium Fluoride → 1-(2,4-Dichloro-3-hydroxymethylphenyl)2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

HRID 613610Notes

Reaction equation

HRID 613610 reaction equation
[Si]([O:18][CH2:19][C:20]1[C:21]([Cl:48])=[C:22]([N:27]2[CH:31]=[CH:30][CH:29]=[C:28]2[CH2:32][NH:33][C:34](=[O:47])[CH:35]=[CH:36][C:37]2[CH:42]=[CH:41][C:40]([C:43](=[O:46])[NH:44][CH3:45])=[CH:39][CH:38]=2)[CH:23]=[CH:24][C:25]=1[Cl:26])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:48][C:21]1[C:20]([CH2:19][OH:18])=[C:25]([Cl:26])[CH:24]=[CH:23][C:22]=1[N:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH2:32][NH:33][C:34](=[O:47])[CH:35]=[CH:36][C:37]1[CH:38]=[CH:39][C:40]([C:43](=[O:46])[NH:44][CH3:45])=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 542764421-[3-(Tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

Product 1

HCID 539366561-(2,4-Dichloro-3-hydroxymethylphenyl)2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrroleYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-[3-(tert-butyldiphenylsilyloxymethyl)-2,4-dichlorophenyl]-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole (620 mg) in tetrahydrofuran (6 ml) was added 1N solution of tetrabutylammonium fluoride in tetrahydrofuran (2.5 ml). The mixture was stirred at ambient temperature for 6 hours and partitioned between ethyl acetate and water. The organic layer was isolated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with 1N hydrochloric acid and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with methanol to give 1-(2,4-dichloro-3-hydroxymethylphenyl)-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole (197 mg) as a brownish powder.

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic layer was isolated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with 1N hydrochloric acid and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-94d933bfc68e468cac3bd52946136483
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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