Sodium borohydride → HCID 19961064, compound

HRID 54143Notes

Reaction equation

HRID 54143 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[C:14]2[C:9](=[C:10]([O:17][CH3:18])[C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH2:8][CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=1)#[N:4]>C(O)C>[C:3]([CH:5]1[C:14]2[C:9](=[C:10]([O:17][CH3:18])[C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH2:8][CH:7]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:6]1)#[N:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 199611621-Cyano-5,6-dimethoxy-3-phenyl-3,4-dihydronaphthalene

Product 1

HCID 19961064HCID 19961064, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (6.8 g) was added to a suspension of 6.8 g (23.3 mmol) of 1-cyano-5,6-dimethoxy-3-phenyl-3,4-dihydronaphthalene, from Step 1, in 100 mL of absolute ethanol and the reaction mixture was heated at reflux temperature for 1.5 h. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with 1N aqueous hydrochloric acid solution, aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to an oil. The oil was triturated with heptane to give 5.63 g (82% yield) of the title compound as a white crystalline solid, m.p. 118°-121° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for 1.5 h
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with 1N aqueous hydrochloric acid solution, aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customThe oil was triturated with heptane

Sources & evidence

ORD record
ord-69dad932ca2345b89109ca7ad0002832
Source dataset
uspto-grants-1997_04
Patent number
US05621133

Reaction notes

Loading…