Aluminium lithium hydride → HCID 22494266, compound

HRID 1042451Notes

Reaction equation

HRID 1042451 reaction equation
CON(C)[C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[O:15][CH2:16][CH2:17][CH3:18].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:16]([O:15][C:6]1[CH:7]=[C:8]([C:11]([F:12])([F:13])[F:14])[CH:9]=[CH:10][C:5]=1[CH:4]=[O:19])[CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86649956HCID 86649956, compound

Product 1

HCID 22494266HCID 22494266, compoundYield 105.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Methoxy-N-methyl-2-propoxy-4-trifluoromethyl-benzamide (277 mg) in THF was reacted with 1 M LAH (1 ml) on −50° C. for 1 hr. The reaction mixture was quenched by adding aqueous potassium hydrogen sulfate (5 ml). The mixture was stirred for 30 min. The reaction solvent was removed in vacuo. Water (30 ml) was added to the resulting residue, which was extracted with ethyl acetate (30 ml×3). The combined organic layer was washed with brine (30 ml) and dried over MgSO4 and concentrated in vacuo to yield title compound (232 mg, 100%).

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding aqueous potassium hydrogen sulfate (5 ml)
  3. customThe reaction solvent was removed in vacuo
  4. additionWater (30 ml) was added to the resulting residue, which
  5. extractionwas extracted with ethyl acetate (30 ml×3)
  6. washThe combined organic layer was washed with brine (30 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52b813e357b340a6915eed574b90b979
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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