Water → [5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazol-4-yl]methanol

HRID 2261321Notes

Reaction equation

HRID 2261321 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:12]2[N:16]([C:17]([CH3:20])([CH3:19])[CH3:18])[N:15]=[CH:14][C:13]=2[C:21](OCC)=[O:22])[CH:11]=[CH:10][CH:9]=[CH:8]1.O>O1CCCC1>[N:7]1([C:12]2[N:16]([C:17]([CH3:18])([CH3:19])[CH3:20])[N:15]=[CH:14][C:13]=2[CH2:21][OH:22])[CH:8]=[CH:9][CH:10]=[CH:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 57736366ethyl 5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazole-4-carboxylate

Product 1

HCID 57736270[5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazol-4-yl]methanolYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.30 g of lithium aluminum hydride was suspended in 50 ml of tetrahydrofuran and thereto, under a nitrogen atmosphere, a solution of 8.95 g of ethyl 5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazole-4-carboxylate in 20 ml of tetrahydrofuran was added dropwise over 15 minutes under ice-cooling. The mixture was stirred for 8 hours under ice-cooling. After water was added, the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 7.06 g of [5-(1H-pyrrol-1-yl)-1-t-butyl-1H-pyrazol-4-yl]methanol.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19bfae681a14486d88e8e029d5d1df07
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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