Hydrochloric Acid → HCID 21770110, compound

HRID 30702Notes

Reaction equation

HRID 30702 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18](OCC)=[O:19])[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([CH2:18][OH:19])[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3764386ethyl 1,5-diphenyl-1H-pyrazole-4-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 21770110HCID 21770110, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of ethyl 1,5-diphenyl-1H-pyrazole-4-carboxylate (14.9 g) and tetrahydrofuran (250 ml) was added dropwise diisobutylaluminum hydride (1 mol/l toluene solution, 120 ml) under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr. and poured into a 1N aqueous hydrochloric acid solution. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with a 1N aqueous hydrochloric acid solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give (1,5-diphenyl-1H-pyrazol-4-yl)methanol (12.6 g, 99%) as colorless crystals. Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 147-148° C.

Workup

  1. temperaturecooling
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed successively with a 1N aqueous hydrochloric acid solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5839447568df45edb9f5c3d4d1ac1059
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

Loading…