Water → HCID 66924088, compound

HRID 1364384Notes

Reaction equation

HRID 1364384 reaction equation
[H-].[Na+].[CH:3]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15](F)[C:12]=1[C:13]#[N:14].O>CN(C=O)C>[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([O:9][CH2:8][CH:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)[C:12]=1[C:13]#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 746952,6-DifluorobenzonitrileHCID 77195Cyclopentanemethanol

Product 1

HCID 66924088HCID 66924088, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60%; 349 mg; 8.7 mmol) was suspended in DMF (3 mL) and cooled to 0° C. under inert atmosphere. Cyclopentylmethanol (0.79 mL; 7.3 mmol) was added dropwise to the sodium hydride mixture. The solution was allowed to warm to room temperature and stirred for 20 minutes. The solution was then added dropwise to a solution of 2,6-difluorobenzonitrile (1.03 g; 7.4 mmol) in DMF (3 mL) cooled to 0° C. The mixture was allowed to warm to room temperature and stirred for 4 hours. The solution was poured over 50 mL of cooled water and extracted with ethyl acetate and solvent removed. Purification by column chromatography (5% ethyl acetate/hexane) yielded 1.66 grams of 2-fluoro-6-(cyclopentylmethoxy)benzonitrile.

Workup

  1. temperatureto warm to room temperature
  2. temperaturecooled to 0° C
  3. temperatureto warm to room temperature
  4. stirringstirred for 4 hours
  5. extractionextracted with ethyl acetate and solvent
  6. customremoved
  7. customPurification by column chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4f36abcdcfac482e9fdb1f7bdf8f1b8e
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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