Diisobutylaluminum hydride → [2-Methoxy-5-(trifluoromethyl)pyridin-3-yl]methanol

HRID 1753207Notes

Reaction equation

HRID 1753207 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:4]=1[C:5](OC)=[O:6].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH2:5][OH:6])=[CH:9][C:10]([C:13]([F:16])([F:14])[F:15])=[CH:11][N:12]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 85982637HCID 85982637, compound

Product 1

HCID 71650743[2-Methoxy-5-(trifluoromethyl)pyridin-3-yl]methanolYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-methoxy-5-(trifluoromethyl)nicotinate (13) (0.5 g, 2.12 mmol) dissolved in DCM was added DIBAL-H (6.38 ml, 1M in Toluene) at 0° C. The reaction mixture was stirred for 2 h at RT. Then the reaction mixture was quenched with saturated NH4Cl solution and extracted with ethyl acetate (2×25 mL). The combined organic layer was washed with water, brine, dried over sodium sulfate, and concentrated at reduced pressure to yield (2-methoxy-5-(trifluoromethyl)pyridin-3-yl)methanol (14) as a pale yellow liquid (0.4 g, 90%).

Workup

  1. customThen the reaction mixture was quenched with saturated NH4Cl solution
  2. extractionextracted with ethyl acetate (2×25 mL)
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-567a33fdf1ab4189a7f088914253a20d
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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