Water → 7-Methoxy-2-naphthonitrile

HRID 412588Notes

Reaction equation

HRID 412588 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](OS(C(F)(F)F)(=O)=O)=[CH:10]2)=[CH:5][CH:4]=1.O.C(OCC)(=O)C.[CH3:28][N:29](C)C=O>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:28]#[N:29])=[CH:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 10892112Methanesulfonic acid, trifluoro-, 7-methoxy-2-naphthalenyl ester

Product 1

HCID 109541837-Methoxy-2-naphthonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
80 °C

Procedure

To a solution of 7-methoxy-2-trifluoromethanesulfonyloxynaphthalene (2.23 g) in dimethylformamide (8.9 ml) were added zinc cyanide (598 mg) and tetrakis(triphenylphosphine) palladium (337 mg) at room temperature, and the mixture was stirred at 80° C. for 1 hour. After completion of the reaction, water and ethyl acetate were added and insoluble material was removed. The organic layer was separated and concentrated, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1) and dried under reduced pressure to give the title compound (965 mg).

Workup

  1. additionwere added
  2. custominsoluble material was removed
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-6e617d586ca3431080af649979ddb30b
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

Loading…