Aluminium lithium hydride → HCID 18386569, compound

HRID 380949Notes

Reaction equation

HRID 380949 reaction equation
[C:1]1([C:7]([NH:20][C:21]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:22]=2[C:23](C[N-]OC)=[O:24])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:1]1([C:7]([NH:20][C:21]2[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:22]=2[CH:23]=[O:24])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86584811HCID 86584811, compound

Product 1

HCID 18386569HCID 18386569, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-triphenylmethylamino-6-fluorobenzoyl N-methoxy-methylamide (300 mg, 0.68 mmol) in THF (4 mL) at −78° C. was added lithium aluminum hydride (30 mg, 0.82 mmol) and the resulting reaction mixture was allowed to stir with warming to room temperature (dry ice bath removed after addition of reagent) for 1 h. The reaction mixture was quenched with 20% KHSO4 and extracted with EtOAc (3×100 mL) and the combined EtOAc extracts were dried over anhydrous NaSO4 and concentrated in vacuo. Chromatography (SiO2, 5% EtOAc-hexanes) provided 182 mg of the title compound (260 mg theoretical, 70% yield).

Workup

  1. customthe resulting reaction mixture
  2. custom(dry ice bath removed after addition of reagent) for 1 h
  3. customThe reaction mixture was quenched with 20% KHSO4
  4. extractionextracted with EtOAc (3×100 mL)
  5. dry with materialthe combined EtOAc extracts were dried over anhydrous NaSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-449307139cb6479fb69701fa54fabe47
Source dataset
uspto-grants-2001_10
Patent number
US06303780B1

Reaction notes

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