Sodium hydride → HCID 67102642, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 13.29 g of triphenylethylvalerate phosphonium bromide and 0.745 g of sodium hydride in 40 ml of DMSO was stirred for 30 min, under nitrogen in a 3-necked, 100 ml round bottom flask equipped with a stir bar, reflux condenser with a nitrogen inlet and a thermocouple. The mixture changed from light yellow to brown and heated to 40.2° C. from 23.2° C. 5.00 g of 3-(2,6-dimethylbenzyloxy)benzaldehyde was dissolved in 20 ml of DMSO and added, dropwise over a 4 min. period to the reaction mixture. The mixture heated to 26.8° C. from 21.8° C. The reaction mixture was stirred and allowed to cool to room temperature. The reaction was analyzed after 1 hr. and LC-MS showed almost all the starting aldehyde left and ˜3% desired product. The reaction mixture was heated to 50° C. and stirred for 3 hrs. The reaction was analyzed after 2 and 3 hrs. LC-MS showed ˜20% starting aldehyde left and 17% desired product. The reaction was cooled to room temperature and placed in a refrigerator overnight.

Provenance & Evidence