Ethyl Acetate → (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(tetradecyloxy)furan-2-carboxylate

To a stirred, room temperature solution of 5-(tetradecyloxy)furan-2-carboxylic acid (0.228 g, 0.70 mmol) in DMF (4 mL) was added potassium carbonate (0.146 g, 1.05 mmol) and 4-(bromomethyl)-5-methyl-1,3-dioxol-2-one (0.160 g, 0.84 mmol). The reaction vessel was capped and stirring was continued for 14 hrs at which time TLC ((20% EtOAc in Hexanes Rf=0.10 (SM) and 0.40 (Prod)) indicated complete consumption of the starting material. The reaction was quenched by the addition of water (5 mL), brine (5 mL) and EtOAc (30 mL). The biphasic mixture was transferred to a seperatory funnel and the organic phase was extracted 3 times with brine (3×10 mL). The organic phase was dried and concentrated to give a colourless oil. The resulting crude material was purified by flash chromatography eluting with 5-20% EtOAc in hexanes to yield a colourless syrup that solidified on standing. 1H NMR (400 MHz, DMSO-d6) δ: 7.2 (d, 1H), 5.6 (d, 1H), 5.1 (s, 2H), 4.1 (t, 2H), 2.18 (s, 3H), 1.6-1.8 (m, 2H), 1.3-1.4 (m, 2H), 1.23 (d, 6H), 1.2 (s, 20H), 0.85 (t, 3H).

1. customThe reaction vessel was capped
2. customconsumption of the starting material
3. customThe reaction was quenched by the addition of water (5 mL), brine (5 mL) and EtOAc (30 mL)
4. customThe biphasic mixture was transferred to a seperatory funnel
5. extractionthe organic phase was extracted 3 times with brine (3×10 mL)
6. customThe organic phase was dried
7. concentrationconcentrated
8. customto give a colourless oil
9. customThe resulting crude material was purified by flash chromatography
10. washeluting with 5-20% EtOAc in hexanes
11. customto yield a colourless syrup that

ORD-Eintrag

ord-925f62bc6a8d4fbf83dbe7638c1244f8

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09434718B2