Pyridine → Methyl 3,3-dimethoxy-1-vinylcyclobutanecarboxylate

Temperatur

0 °C

To a solution of methyl 1-(1-hydroxyethyl)-3,3-dimethoxycyclobutanecarboxylate (3.28 g, 15.03 mmol) and pyridine (2.4 mL, 29.83 mmol) in CH2Cl2 (65 mL) was added trifluoromethanesulfonic anhydride (3.0 mL, 17.86 mmol) at −78° C. The mixture was stirred for 10 minutes and then warmed to 0° C. After stirring for 15 minutes at 0° C., DBU (9.0 mL, 60.18 mmol) was added to the reaction mixture and the resulting mixture was stirred for 1 hour at room temperature. The mixture was partially evaporated under reduced pressure and filtrated through the pad of silica gel and washed with CH2Cl2. The filtrate was washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered, and evaporated. The residue was diluted with hexane/EtOAc=4:1 and added small amount of CHCl3 and filtrated through the pad of silica gel to give methyl 3,3-dimethoxy-1-vinylcyclobutanecarboxylate (2.21 g).

1. stirringAfter stirring for 15 minutes at 0° C.
2. stirringthe resulting mixture was stirred for 1 hour at room temperature
3. customThe mixture was partially evaporated under reduced pressure
4. filtrationfiltrated through the pad of silica gel
5. washwashed with CH2Cl2
6. washThe filtrate was washed with saturated aqueous NaHCO3
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. customevaporated
10. additionThe residue was diluted with hexane/EtOAc=4:1
11. additionadded small amount of CHCl3
12. filtrationfiltrated through the pad of silica gel

ORD-Eintrag

ord-502ebe170fed4f34b3f2352c5ea8d056

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09242973B2