Sodium Cyanide → (3'-Benzyloxybiphenyl-2-yl)acetonitrile

HRID 278178Notes

Reaction equation

HRID 278178 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10]=1.[C-:23]#[N:24].[Na+]>CCO.O>[CH2:16]([O:15][C:11]1[CH:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:2][C:23]#[N:24])[CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 226271042-Chloromethyl-3'-benzyloxybiphenyl

Product 1

HCID 22627114(3'-Benzyloxybiphenyl-2-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2-chloromethyl-3′-benzyloxybiphenyl from Step A (188 mg, 0.61 mmol) in EtOH (4 mL) was added a solution of NaCN (60 mg, 1.22 mmol) in water (4 mL). The resulting solution was heated to reflux for 12 h, stood at ambient temperature for 48 h, then concentrated under reduced pressure. The residue was partitioned between sat. aq. NaHCO3 (10 mL) and CH2Cl2 (20 mL). The aqueous layer was extracted further with CH2Cl2 (2×10 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with a gradient of 2-10% EtOAc in hexane to give the titled product.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 12 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between sat. aq. NaHCO3 (10 mL) and CH2Cl2 (20 mL)
  5. extractionThe aqueous layer was extracted further with CH2Cl2 (2×10 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash column chromatography
  10. washeluting with a gradient of 2-10% EtOAc in hexane

Sources & evidence

ORD record
ord-a7f4d6cc4c99400caa89029dab7308ad
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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