Diisobutylaluminum hydride → (1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazol-5-yl)methanol

HRID 2261741Notes

Reaction equation

HRID 2261741 reaction equation
C[O:2][C:3]([C:5]1[N:6]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])[N:7]=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11])=O.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:20])[C:13]=1[N:6]1[C:5]([CH2:3][OH:2])=[C:9]([CH:10]([CH3:12])[CH3:11])[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 574432552-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 57443256(1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazol-5-yl)methanolYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazole-3-carboxylic acid methyl ester (2.2 g, 6.8 mmol) in THF (30 mL) is added DIBAL-H (33.7 mL, 1M in toluene). The reaction mixture is stirred at ambient temperature overnight. The reaction is quenched by the addition of methanol and is concentrated under reduced pressure. The residue is partitioned between 5N NaOH and EtOAc. The layers are separated and the organic layer is filtered through a pad of diatomaceous earth. The filtrate is concentrated under reduced pressure to give the title compound as a light yellow solid, (1.6 g, 80%). 1H NMR (400 MHz, CDCl3): δ 7.67 (s, 1H), 7.44 (d, 2H), 7.34 (dd, 1H), 4.45 (s, 2H), 3.00 (m, 1H), 1.32 (d, 6H).

Workup

  1. customThe reaction is quenched by the addition of methanol
  2. concentrationis concentrated under reduced pressure
  3. customThe residue is partitioned between 5N NaOH and EtOAc
  4. customThe layers are separated
  5. filtrationthe organic layer is filtered through a pad of diatomaceous earth
  6. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-41b261c9f6d041d9add01532e368ddd8
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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