Diisobutylaluminumhydride → 2-(4-fluorophenyl)4-hydroxymethyl-3-(pyridin-4-yl)-1H-pyrrole

HRID 1244978Notes

Reaction equation

HRID 1244978 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[C:17]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[C:18]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[NH:19][CH:20]=1)=O)C>C1(C)C=CC=CC=1.O1CCCC1>[F:27][C:24]1[CH:23]=[CH:22][C:21]([C:18]2[NH:19][CH:20]=[C:16]([CH2:14][OH:13])[C:17]=2[C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 219228384-Ethoxycarbonyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole

Product 1

HCID 219227712-(4-fluorophenyl)4-hydroxymethyl-3-(pyridin-4-yl)-1H-pyrroleYield 99.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

121.4 ml (121.4 mmol) of a 1M solution of diisobutylaluminium hydride in toluene were slowly added dropwise to a solution of 12.56 g (40.47 mmol) of 4-ethoxycarbonyl-2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole [which was obtained in step (i) above] in 630 ml of tetrahyrofuran with ice-cooling. After completing the addition, the cooling bath was removed and the mixture was stirred at room temperature for 5 hours. At the end of this time, a saturated aqueous solution of ammonium chloride was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure to give 10.80 g (yield 99%) of the title compound as a pale orange powder.

Workup

  1. temperaturecooling
  2. additionthe addition
  3. customthe cooling bath was removed
  4. additionAt the end of this time, a saturated aqueous solution of ammonium chloride was added to the reaction mixture
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-5f2cb99152cf480988fd8f7929371521
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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