Sodium borohydride → HCID 19961064, compound

HRID 1089024Notes

Reaction equation

HRID 1089024 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, compound

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-3,4-dihydro-5,6-dimethoxy-3-phenyl naphthalene, 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. customtriturated" with heptane

Sources & evidence

ORD record
ord-7827e6b1d3744490a9dcb0ba45a32e49
Source dataset
uspto-grants-1990_10
Patent number
US04963568

Reaction notes

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