Sodium borohydride → 1-Cyano-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene

HRID 982123Notes

Reaction equation

HRID 982123 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[C:14]2[C:9](=[C:10]([O:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=1)#[N:4]>C(O)C>[C:3]([CH:5]1[C:14]2[C:9](=[C:10]([O:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:6]1)#[N:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 200690311-Cyano-5-methoxy-3-phenyl-3,4-dihydronaphthalene

Product 1

HCID 200690891-Cyano-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (6.8 g) is added to a suspension of 6.1 g (23.3 mmol) of 1-cyano-5-methoxy-3-phenyl-3,4-dihydronaphthalene, from Step 1, in 100 mL of absolute ethanol and the reaction mixture is heated at reflux temperature for 1.5 h. The solvent is evaporated under reduced pressure and the residue partitioned between equal volumes of ethyl acetate and 1N aqueous hydrochloric acid solution. The layers are separated and the organic layer is washed with aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give the title compound.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux temperature for 1.5 h
  3. customThe solvent is evaporated under reduced pressure
  4. customthe residue partitioned between equal volumes of ethyl acetate and 1N aqueous hydrochloric acid solution
  5. customThe layers are separated
  6. washthe organic layer is washed with aqueous sodium bicarbonate solution and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-fc69a76d38e74bae923d81571868dadd
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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