Water → HCID 43180303, compound

HRID 2176977Notes

Reaction equation

HRID 2176977 reaction equation
[H-].[Na+].F[C:4]1[CH:11]=[CH:10][CH:9]=[C:8](F)[C:5]=1[C:6]#[N:7].[OH2:13].CN([CH:17]=[O:18])C>>[O:13]1[CH2:10][CH2:11][CH2:4][CH2:5][CH:6]1[CH2:17][O:18][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 43180303HCID 43180303, compound

Conditions

Temperature
0 °C

Procedure

To a mixture of 60% sodium hydride (0.160 g; 4.00 mmol) in DMF (5 mL) at 0° C. was added dropwise (2-hydroxymethyl)tetrahydropyran (0.465 g; 4.00 mmol) and the mixture was stirred at 0° C. for 30 minutes. The mixture was added to a solution of 2,6-difluorobenzonitrile (0.556 g, 4.00 mmol) in DMF (5 mL) at 0° C. and stirred for 18 hours at ambient temperature. The solution was poured into a mixture of ice and water, and extracted with ethyl acetate. The organic layer was washed with water and then brine, dried over magnesium sulfate, and solvent removed. Purification by column chromatography (CH2Cl2) to yield 0.587 grams of 2-(tetrahydropyran-2-ylmethoxy)benzonitrile.

Workup

  1. stirringstirred for 18 hours at ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine, dried over magnesium sulfate, and solvent
  5. customremoved
  6. customPurification by column chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-4e62d95554d5491298c94ab4173c6f97
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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