Water → HCID 71279132, compound

HRID 1621176Notes

Reaction equation

HRID 1621176 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:6][C:7]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[C-:20]#[N:21].[K+].O>CS(C)=O>[C:14]1([C:5]2[O:6][C:7]([C:8]3[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=3)=[C:3]([CH2:2][C:20]#[N:21])[N:4]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 86677498HCID 86677498, compound

Product 1

HCID 71279132HCID 71279132, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-(chloromethyl)-2-phenyl-5-(pyridin-3-yl)oxazole (197 mg, 728 μmol) in DMSO (4 mL) was added at RT potassium cyanide (56.9 mg, 873 μmol). Stirring was continued for 1 h and the reaction mixture was poured into water (25 mL) and extracted with ethyl acetate (2×50 mL). The organic phases were washed with water (2×20 mL) and brine (1×20 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give 168 mg crude product. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as light yellow solid (80 mg, 306 μmol, 42.1%).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe organic phases were washed with water (2×20 mL) and brine (1×20 mL)
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0046baf68cba4f168a77d6f11ce64bc4
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

Loading…