Diisobutylaluminumhydride → HCID 68785918, compound

HRID 2265962Notes

Reaction equation

HRID 2265962 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[C:6]([C:7](OC)=[O:8])=[CH:5][N:4]=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([CH2:7][OH:8])=[C:11]([C:13]([F:16])([F:14])[F:15])[CH:12]=1

Participants

4

Reactant 2

HCID 21225700Diisobutylaluminumhydride2×HCID 68783523HCID 68783523, compound

Product 1

HCID 68785918HCID 68785918, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a cooled (−78° C.) solution of methyl 6-methoxy-4-trifluoromethylnicotinate (300 mg, 1.35 mmol) in toluene (10 mL) was added diisobutylaluminum hydride (DIBAL, 1 M/toluene, 1.35 mL). The mixture was warmed slowly to room temperature and stirred for 2 days. Additional DIBAL (1 M/toluene, 2 mL) was added to complete the reaction. After stirring for 4 hours, the mixture was quenched with saturated aqueous ammonium chloride solution (1 mL), dried over anhydrous magnesium sulfate, filtered through a pad of celite, and concentrated under reduced pressure to give 6-methoxy-4-trifluoromethyl-3-pyridinemethanol (220 mg, 78.6%). The crude product was used directly in the following Swern oxidation.

Workup

  1. customthe reaction
  2. stirringAfter stirring for 4 hours
  3. customthe mixture was quenched with saturated aqueous ammonium chloride solution (1 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered through a pad of celite
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f923b99b776943038d32ebd1e803ac53
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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