Ethylene glycol monoallyl ether → Methyl (2-allyloxy-ethoxy)-acetate

Temperature

0 °C

To a stirred solution of 2-allyloxy-ethanol 7 (10.9 mL, 100 mmol, 1.0 equiv.) in THF (200 mL) was carefully added NaH (60%, 4.8 g, 120 mmol, 1.2 equiv.) in small portions at room temperature. The reaction was then refluxed for 1 h (until H2 release ceased) then cooled to 0° C. Methyl bromoacetate (11.4 mL, 120 mmol, 1.2 equiv.) was then added dropwise. After 15 min at 0° C., the reaction was submitted to a EtOAc/H2O extraction. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered then evaporated under reduced pressure. Purification was achieved by Kugelrohr distillation under reduced pressure and provided 9.77 g (55%) of ester (8) as a colorless oil; bp=130-145° C. (water tap vacuum); 1H NMR (400 MHz, CDCl3) δ 5.91 (m, 1H), 5.28 (m, 1H), 4.99 (m, 1H), 4.19 (s, 2H), 4.02 (m, 2H), 3.76 (s, 3H), 3.75 (m, 2H), 3.64 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 171.1, 134.8, 117.3, 72.4, 71.2, 69.7, 68.9, 51.9; IR (neat) 1755 cm−1; HRMS (ESI, m/z) calcd. for C8H15O4 (MH+) 175.0964. found 175.0960.

1. customat room temperature
2. temperatureThe reaction was then refluxed for 1 h (until H2 release ceased)
3. extractionthe reaction was submitted to a EtOAc/H2O extraction
4. washThe combined organic layers were washed with brine
5. dry with materialdried over anhydrous MgSO4
6. filtrationfiltered
7. customthen evaporated under reduced pressure
8. customPurification
9. distillationwas achieved by Kugelrohr distillation under reduced pressure

ORD record

ord-8050a2904c5544e78fe3396067ad33cd

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08491958B2