Potassium Carbonate → 4-(Oxiran-2-yl)benzonitrile

HRID 1596454Notes

Reaction equation

HRID 1596454 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9](=[O:12])[CH2:10]Br)=[CH:7][CH:6]=1)#[N:4].C([O-])([O-])=O.[K+].[K+]>C1COCC1.CC#N>[O:12]1[CH2:10][CH:9]1[C:8]1[CH:13]=[CH:14][C:5]([C:3]#[N:4])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 986544-(Bromoacetyl)benzonitrileHCID 4311764Sodium borohydride

Product 1

HCID 404944-(Oxiran-2-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (1.6 g; 40 mmol) was added to a stirred solution of 4-cyanophenacyl bromide (8.8 g; 40 mmol) in THF (100 mL), and the reaction mixture was stirred until tic indicated that the reaction was complete. The solvent was evaporated and the residue partitioned between DCM and H2O, and the organic layer was separated, dried and concentrated. The residue was treated with K2CO3 (0.08 mol) in MeCN (85 mL) at room temperature overnight. The solvent was removed on a rotary evaporator and the residue partitioned between CH2Cl2 and H2O. The organic layer was washed with H2O (2×100 mL), separated and dried to give the sub-title compound in 90% overall yield.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between DCM and H2O
  3. customthe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe solvent was removed on a rotary evaporator
  7. customthe residue partitioned between CH2Cl2 and H2O
  8. washThe organic layer was washed with H2O (2×100 mL)
  9. customseparated
  10. customdried

Sources & evidence

ORD record
ord-7be36e81b2a94ece83579611404db1f9
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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