Diisobutylaluminum hydride → HCID 117818791, compound

HRID 1753212Notes

Reaction equation

HRID 1753212 reaction equation
[F:1][C:2]1[C:3]([CH3:14])=[N:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:11]=[C:6]([CH2:7][OH:8])[C:5]([O:12][CH3:13])=[N:4][C:3]=1[CH3:14]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 117818878HCID 117818878, compound

Product 1

HCID 117818791HCID 117818791, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 5-fluoro-2-methoxy-6-methylnicotinate (19) (0.25 g, mmol) in MDC was added DIBAL-H in dropwise (2.5 ml, 1M in Toluene) at 0° C. The reaction mixture was stirred for 2 h at RT. Reaction was quenched with saturated ammonium chloride solution and extracted with DCM (2×50 ml). The combined organic layer was washed with water, brine and solvent was evaporated under reduced pressure to yield (5-fluoro-2-methoxy-6-methylpyridin-3-yl)methanol (20) as a liquid (0.2 g 90%).

Workup

  1. customReaction
  2. customwas quenched with saturated ammonium chloride solution
  3. extractionextracted with DCM (2×50 ml)
  4. washThe combined organic layer was washed with water, brine and solvent
  5. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-2c962abc930b4f39a7d940bf89fa8689
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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