Sodium → HCID 178467284, compound

Participants

Reaction Conditions

Reaction Steps

To a flask containing 30 mL dry MeOH was added sodium metal (1.00 g, 43.5 mmol, 3.4 eq.). The mixture was stirred vigorously until sodium is dissolved. To a pressure vessel containing 31F (4.81 g, 12.9 mmol, 1.0 eq.) in MeOH (50 mL) was added the freshly prepared NaOMe solution. The pressure vessel was sealed and heated at 100° C. overnight. LC/MS analysis showed the product as the major signal. The reaction mixture was concentrated and then diluted with methylene chloride (500 mL) and aqueous 1 N NH4Cl (100 mL). The organic phase was further washed with aqueous 1 N NH4Cl (100 mL) and saturated aqueous NaCl (100 mL). The combined aqueous phases were extracted with methylene chloride (2×75 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated to give a dark yellow solid 31G which was deemed pure enough to take on to the next reaction without further purification (2.05 g, 49%). ESI-MS: m/z 328.2 (M+H)+

Provenance & Evidence