Sodium → HCID 178467284, compound

Temperature

100 °C

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)+

1. dissolutionis dissolved
2. customThe pressure vessel was sealed
3. concentrationThe reaction mixture was concentrated
4. additiondiluted with methylene chloride (500 mL) and aqueous 1 N NH4Cl (100 mL)
5. washThe organic phase was further washed with aqueous 1 N NH4Cl (100 mL) and saturated aqueous NaCl (100 mL)
6. extractionThe combined aqueous phases were extracted with methylene chloride (2×75 mL)
7. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-659af8254f2b4fc0bd2c71a44b1cf4e4

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071766B2