Sodium hydride → Methyl(2-(2-allyloxy-ethoxy)-ethoxy)-acetate

Temperatur

0 °C

To a stirred solution of alcohol (9) (4.86 g, 33.2 mmol, 1.0 equiv.) in THF (70 mL) was carefully added NaH (60%, 1.60 g, 40.0 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 (3.8 mL, 40.1 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 phases were washed with brine, dried over anhydrous Na2SO4, filtered then evaporated under reduced pressure. Purification was achieved by distillation under high vacuum and provided 4.68 g (64%) of ester (14) as a colourless oil; bp=130-140 0° C. (0.09 Torr); 1H NMR (300 MHz, CDCl3) δ 5.91 (m, 1H), 5.28 (m, 1H), 5.18 (m, 1H), 4.17 (s, 2H), 4.02 (m, 2H), 3.75 (s, 3H), 3.75-3.58 (m, 8H); 13C NMR (75 MHz, CDCl3) δ 171.0, 134.8, 117.1, 72.3, 71.0, 70.8, 70.7, 69.5, 68.7, 51.8; IR (neat) 1754 cm−1; HRMS (ESI, m/z) calcd. for C10H19O5 (MH+) 219.1236, found 219.1227.

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 phases were washed with brine
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. customthen evaporated under reduced pressure
8. customPurification
9. distillationwas achieved by distillation under high vacuum

ORD-Eintrag

ord-df7cf8b013e5482aa7098e89ff25e6a7

Quelldatensatz

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09078956B2