Reaction #2329013

Reaction equation

2-Chloro-4-(cis-2-hydroxy-cyclopentyloxy)-benzonitrile

methyl iodide

→

title compound

Yield 43.5%

2-Chloro-4-(cis-2-methoxy-cyclopentyloxy)-benzonitrile

Yield 43.5%

Conditions

Workup

1. 1
   Dryingdried round bottom flask under nitrogen containing 2 mL of dry DMF and 8.5 mg of 60% sodium hydride as an oil dispersion (0.35 mmol)
2. 2
   workup.STIRRINGThe mixture was stirred for 16 h
3. 3
   Otherquenched by the dropwise addition of 5 mL of water
4. 4
   Extractionextracted with ether (2×)
5. 5
   WashThe combined organic phases were washed with brine
6. 6
   Dryingdried (MgSO4)
7. 7
   Concentrationconcentrated
8. 8
   Otherpurified by reverse phase HPLC (Shimadzu)

Procedure

2-Chloro-4-(cis-2-hydroxy-cyclopentyloxy)-benzonitrile (76 mg, 0.32 mmol) was added to a flame dried round bottom flask under nitrogen containing 2 mL of dry DMF and 8.5 mg of 60% sodium hydride as an oil dispersion (0.35 mmol). The reaction was stirred at room temperature for 1 h, after which time methyl iodide (54 mg, 0.38 mmol) was added. The mixture was stirred for 16 h, quenched by the dropwise addition of 5 mL of water, and extracted with ether (2×). The combined organic phases were washed with brine, dried (MgSO4), concentrated and purified by reverse phase HPLC (Shimadzu) to give 35 mg of the title compound. GC/MS: 251 (M/Z for C13H14ClNO2)—

Source