Aluminium lithium hydride → HCID 66875369, compound

HRID 516866Notes

Reaction equation

HRID 516866 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[F:17])[C:9](OCC)=[O:10].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:9][OH:10])[CH:14]=[CH:15][C:16]=1[F:17]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66692571HCID 66692571, compound

Product 1

HCID 66875369HCID 66875369, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The solution of Ethyl 3-(2,6-dimethylbenzyloxy)-4-fluorobenzoate (Step A, 4.2 g, 13.9 mmol) in dry THF (20 ml) was added slowly to a suspension of LiAlH4 (0.72 g) in dry THF (20 ml) at −78° C. under argon. The cold bath was replaced by ice bath and the reaction mixture was left to stir for 3 hours or until reaction is complete, quenched very slowly with ice and diluted with ethyl acetate. The organic layer was washed with 0.1N HCl, brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (hexane:ethyl acetate, 5:1) to give the title compound.

Workup

  1. customThe cold bath was replaced by ice bath
  2. waitthe reaction mixture was left
  3. customquenched very slowly with ice
  4. additiondiluted with ethyl acetate
  5. washThe organic layer was washed with 0.1N HCl, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography on a silica gel column (hexane:ethyl acetate, 5:1)

Sources & evidence

ORD record
ord-973ccba9a1474fbab6ed4034492fba00
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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