Sodium Azide → HCID 10749271, compound

Temperature

-20 °C

To the solution of NaN3 (2.80 g, 43.01 mmol) in 100 ml of DMF at −20° C. was added methyl 4-bromocrotonate (5.00 ml, 85%, 36.10 mmol). After stirred at −20° C. for 30 min, the mixture was stirred at 0° C. for 4 h, evaporated, suspended with EtAc/Hexane (1:1), filtered, evaporated and chromatographic purification on SiO2 column eluted with EtAc/Hexane (1:25 to 1:10) to afford HRMS for 4.08 g (80%) of the title product. 1H NMR (CDCl3) 6.88 (m, 1H), 6.06 (ddd, 1H, J=1.7, 3.4, 15.6 Hz), 3.97 (dd, 2H, J=1.2, 4.96 Hz), 3.73 (s, 3H); 13C NMR 166.23, 140.86, 123.49, 51.95, 51.36; ESI MS m/z+182.5 (M+Na+H2O); HRMS m/z+(C5H7N3O2+H2O+Na) calcd 182.0542. found 182.0548.

1. stirringthe mixture was stirred at 0° C. for 4 h
2. customevaporated
3. filtrationfiltered
4. customevaporated
5. customchromatographic purification on SiO2 column
6. washeluted with EtAc/Hexane (1:25 to 1:10)

ORD record

ord-ef184045ecc545909be3a206b9ab6850

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09061995B2