Diethyl Ether → HCID 14439127, compound

Participants

Reaction Steps

Vinyl-terminated phenyl pyrimidines with different spacer lengths were synthesized from 4-(5-decylpyrimidin-2-yl)phenol for siloxane coupling to 1,2 polybutadiene. A general procedure for this synthesis is as follows: 4-(5-decylpyrimidin-2-yl)phenol (1.89 grams, 6.05 mmols), a bromoalkene (7-bromo hept-1-ene, 8-bromooct-1-ene or 10-bromododec-1-ene, 8 mmol) and Cs2CO3 (2.56 grams, 8 mmols) were stirred at room temperature in 40 mL of dimethyl formamide overnight, resulting in near-quantitative conversion to the ether (Scheme 3), monitored by thin layer chromatography. The reaction mixture was extracted three times with 50 mL of dichloromethane. The organic extracts were washed three times with water and dried with MgSO4. The crude product was recrystallized in hot 95% ethanol, resulting in analytically pure white crystals of 5-decyl-2-(4-(hept-6-enyloxy)phenyl)pyrimidine, 5-decyl-2-(4-(oct-7-enyloxy)phenyl)pyrimidine, -decyl-2-(4-(dec-9-enyloxy)phenyl)pyrimidine (1.20 g, 2.09 g, 1.69 g AND 48.0%, 83.6%, 66.02% overall yield, respectively).

Provenance & Evidence