Diisobutylaluminum hydride → HCID 21935631, compound

HRID 1242341Notes

Reaction equation

HRID 1242341 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)=[N:6][C:5]=1[CH3:21].CC(C[AlH]CC(C)C)C>C1COCC1>[CH3:21][C:5]1[C:4]([CH2:3][OH:2])=[CH:9][CH:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:19])([F:18])[F:20])=[CH:12][CH:11]=2)[N:6]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 670722682-Methyl-6-(4-trifluoromethoxy-phenyl)-nicotinic acid methyl ester

Product 1

HCID 21935631HCID 21935631, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.54 g (4.95 mmol) of the above synthesized 2-methyl-6-(4-trifluoromethoxy-phenyl)-nicotinic acid methyl ester in 25 ml of abs. THF was cooled down to −20° C. and reacted with 14.84 ml of DIBAL-H-solution (1.0 M in toluene, 3 eq.) for 0.5 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, hexane/AcOEt=1/1) to deliver finally 0.877 g of the title compound as off-white solid of mp. 68–69° C.

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, hexane/AcOEt=1/1)

Sources & evidence

ORD record
ord-8e38255349a9474584f30de784a942a3
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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