Sodium hydride → HCID 66924353, compound

HRID 2176994Notes

Reaction equation

HRID 2176994 reaction equation
[H-].[Na+].[C:3]12([CH2:13][OH:14])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20](F)[C:17]=1[C:18]#[N:19]>CN(C=O)C>[C:3]12([CH2:13][O:14][C:20]3[CH:21]=[CH:22][CH:23]=[C:16]([F:15])[C:17]=3[C:18]#[N:19])[CH2:10][CH:9]3[CH2:8][CH:7]([CH2:6][CH:5]([CH2:11]3)[CH2:4]1)[CH2:12]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 66924353HCID 66924353, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a cold (ice water) suspension of sodium hydride (206 mg; 5.0 mmol) in anhydrous DMF (4 mL) is added a solution of 1-adamantane methanol (830 mg; 4.9 mmol) in anhydrous DMF (5 mL) over 10 minutes. After allowing to room temperature over 40 minutes, this solution is added to a cold (ice water) stirred solution of 2,6-difluorobenzonitrile (702 mg; 5.0 mmol) in anhydrous DMF (3 mL), and allowed to room temperature over 3 hours. The reaction mixture is poured into ice water with vigorous stirring and extracted with ethyl acetate. The organics are separated and dried over magnesium sulfate. The solvent is removed and the resulting solid is dried under vacuum at 40° C. for 3 hours to give 1.32 grams of 2-(adamantan-1-ylmethoxy)-6-fluorobenzonitrile.

Workup

  1. waitallowed to room temperature over 3 hours
  2. extractionextracted with ethyl acetate
  3. customThe organics are separated
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed
  6. customthe resulting solid is dried under vacuum at 40° C. for 3 hours

Sources & evidence

ORD record
ord-da3a6e6c3d4d476e9b9ca1e9ae0cd3df
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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