4-(Benzyloxy)-3-[4-(benzyloxy)butoxy]benzonitrile → HCID 23143889, compound

HRID 1713295Notes

Reaction equation

HRID 1713295 reaction equation
C([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22]CC1C=CC=CC=1)C1C=CC=CC=1>FC(F)(F)C(O)=O.CSC.O>[OH:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22]

Participants

5

Reactant 1

HCID 231438604-(Benzyloxy)-3-[4-(benzyloxy)butoxy]benzonitrile

Product 1

HCID 23143889HCID 23143889, compoundYield 46.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1068Dimethyl SulfideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-Benzyloxy-3-(4-benzyloxybutoxy)benzonitrile (4.0 g) was dissolved in a mixed solvent of trifluoroacetic acid (9 mL), dimethyl sulfide (0.5 mL) and water (5 mL), and the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5) to give the title compound (1.0 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-81011ce5111a494591ee147b2de3006b
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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