Diisobutylaluminum hydride → HCID 21935719, compound

HRID 1242359Notes

Reaction equation

HRID 1242359 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)=O.CC(C[AlH]CC(C)C)C>C1COCC1>[F:20][C:17]([F:18])([F:19])[C:14]1[CH:13]=[CH:12][C:11]([C:8]2[N:7]=[N:6][C:5]([CH2:3][OH:2])=[CH:10][CH:9]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 67072130HCID 67072130, compound

Product 1

HCID 21935719HCID 21935719, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.582 g (2.062 mmol) of the above prepared 6-(4-trifluoromethyl-phenyl)-pyridazine-3-carboxylic acid methyl ester in 20 ml of abs. THF was cooled down to −15° C. and reacted with 5.16 ml of DIBAL-H-solution (1.0 M in toluene, 2.5 eq.) for ½ h. Careful quenching with ice/HCl dil., twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents left a crude product which was purified by flash chromatography (SiO2, AcOEt) to yield 0.155 g of the title compound as light brown solid.

Workup

  1. customCareful quenching with ice/HCl dil., twofold extraction with AcOEt
  2. washwashing with water
  3. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  4. waitleft a crude product which
  5. customwas purified by flash chromatography (SiO2, AcOEt)

Sources & evidence

ORD record
ord-728ee39493af458cb5f1d02601f0f630
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

Loading…