Diisobutylaluminumhydride → [1-(2,6-dichloro-4-trifluoromethylphenyl)-3,5-diethyl-1H-pyrazol-4-yl]methanol

HRID 1740096Notes

Reaction equation

HRID 1740096 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([CH2:18][CH3:19])=[C:16]([C:20](OC)=[O:21])[C:15]([CH2:24][CH3:25])=[N:14]1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.C1(C)C=CC=CC=1>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[C:17]([CH2:18][CH3:19])=[C:16]([CH2:20][OH:21])[C:15]([CH2:24][CH3:25])=[N:14]1

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 21837355Methyl 1-(2,6-dichloro-4-trifluoromethylphenyl)-3,5-diethylpyrazole4-carboxylate

Product 1

HCID 21837337[1-(2,6-dichloro-4-trifluoromethylphenyl)-3,5-diethyl-1H-pyrazol-4-yl]methanolYield 46%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 8 g (20 mmol) of the compound of step B in 50 mL of tetrahydrofuran (THF) was treated at 0° C. with 44.1 mL of 1.5 M diisobutylaluminum hydride in toluene solution over a period of 5 minutes. The reaction was stirred for 2 hours at 0° C. and was then cautiously quenched with water. The product was extracted into ethyl acetate and dried and evaporated to give the title compound in 46% yield. 1H-NMR (CDCl3) δ 1.04 (3H, t, J=7), 1.26 (3H, t, J=7), 2.44 (2H, q, J=7), 2.70 (2H, q, J=7), 4.54 (2H, s), 7.66 (2H, s).

Workup

  1. customwas then cautiously quenched with water
  2. extractionThe product was extracted into ethyl acetate
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-6cdf895737944d4383206918a2f84f02
Source dataset
uspto-grants-1999_10
Patent number
US05968944

Reaction notes

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