Water → HCID 28782266, compound

HRID 1364396Notes

Reaction equation

HRID 1364396 reaction equation
[H-].[Na+].[CH3:3][C:4]1[O:8][N:7]=[C:6]([CH2:9][OH:10])[CH:5]=1.F[C:12]1[CH:19]=[CH:18][CH:17]=[C:16](F)[C:13]=1[C:14]#[N:15].O>CN(C=O)C>[CH3:3][C:4]1[O:8][N:7]=[C:6]([CH2:9][O:10][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[C:14]#[N:15])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 746952,6-DifluorobenzonitrileHCID 2736567(5-Methyl-1,2-oxazol-3-yl)methanol

Product 1

HCID 28782266HCID 28782266, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 60% sodium hydride (0.164 g; 4.10 mmol) in DMF (5 mL) at 0° C. was added dropwise (5-methylisoxazol-3-yl)methanol (0.456 g; 4.00 mmol) and 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. The solid was collected by filtration and dried in a 40° C. vacuum oven to yield 540 milligrams of (5-methylisoxazole-3-ylmethoxy)benzonitrile.

Workup

  1. stirringstirred for 18 hours at ambient temperature
  2. filtrationThe solid was collected by filtration
  3. customdried in a 40° C. vacuum oven

Sources & evidence

ORD record
ord-217269022ee5464da535550955ccced8
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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