Ethanol → HCID 22996179, compound

HRID 1167323Notes

Reaction equation

HRID 1167323 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][CH3:12])=[C:7]([CH:10]=1)[C:8]#[N:9].C(=O)([O-])[O-].[K+].[K+].[CH2:19]([OH:21])[CH3:20]>>[CH2:19]([O:21][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][CH3:12])=[C:7]([CH:10]=1)[C:8]#[N:9])[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 229961915-(Chloromethyl)-2-methoxybenzonitrile

Product 1

HCID 22996179HCID 22996179, compoundYield 68%

Procedure

To a solution of 5-chloromethyl-2-methoxy-benzonitrile (254 mg, 1.399 mmol) in ethanol (10 mL) was added potassium carbonate (387 mg, 2.798 mmol). The mixture was heated at reflux for 12 h. Upon cooling to room temperature, the solvent was removed. Water (2-5 mL) was added and the product was extracted with diethyl ether (2×20 mL). The organic layers were washed with brine (1×5 mL) and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 20% ethyl acetate in hexanes yielded 5-ethoxymethyl-2-methoxy-benzonitrile (182 mg, 68%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. customthe solvent was removed
  4. additionWater (2-5 mL) was added
  5. extractionthe product was extracted with diethyl ether (2×20 mL)
  6. washThe organic layers were washed with brine (1×5 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe solid was then filtered off
  9. concentrationthe filtrate was concentrated in vacuo
  10. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  11. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-91b60f5c93334c08b4f2792774c95ec3
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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