Aluminium lithium hydride → HCID 11275144, compound

HRID 2172639Notes

Reaction equation

HRID 2172639 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([CH3:11])[C:5]=1[F:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:12][C:5]1[C:6]([CH3:11])=[C:7]([F:10])[CH:8]=[CH:9][C:4]=1[CH2:3][OH:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 44558846Methyl 2,4-difluoro-3-methylbenzoate

Product 1

HCID 11275144HCID 11275144, compoundYield 126.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,4-difluoro-3-methyl-benzoic acid methyl ester from Step A (1.1 g, 5.5 mmol) in tetrahydrofuran (10 mL), cooled to −78° C. using a dry ice/acetone bath, was added lithium aluminum hydride, 1.0M in tetrahydrofuran (10 mL, 10 mmol), in a dropwise manner. The solution was stirred for two hours. The reaction was quenched by dropwise addition of ice-cold saturated sodium bicarbonate solution and was extracted with ethyl acetate. The organic layer was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the alcohol as a colorless liquid (1.1 g, quantitative yield).

Workup

  1. customThe reaction was quenched by dropwise addition of ice-cold saturated sodium bicarbonate solution
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe slurry was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ff6f52e7ceea40c0b490744674a50473
Source dataset
uspto-grants-2015_06
Patent number
US09056110B2

Reaction notes

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