2,5-Dihydrofuran → HCID 68282318, compound

Temperature

23 °C

To a solution of freshly distilled 2,5-dihydrofuran (700 mg, 0.740 mL, 10 mmol), in a mixture of dry 1,3-propanediol/dimethoxyethane (1:1, 5 mL) at 0° C. under argon, were successively added NH4OAc (77 mg, 1 mmol), followed by N-iodosuccinimide (11 mmol, 2.47 g). The mixture was warmed to 23° C. and stirred for 12 h protected from light. The reaction was quenched by addition of sat. aq. Na2SO3 then diluted with water. The mixture was extracted with Et2O/EtOAc (1:1). The combined organic phase was dried (Na2SO4), filtered, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel using hexanes/EtOAc (4:1, 3:1 then 2.5:1) to give iodoalcohol 23 (1.2 g, 45%) as a pale yellow oil. TLC: Rf=0.3 (hexanes/EtOAc=1:1); 1H NMR (CDCl3, 400 MHz) δ 4.33 (m, 1H), 4.29-4.19 (m, 3H), 4.04 (dd, J=2.2, 9.8 Hz, 1H), 3.79 (dd, J=1.5, 9.8 Hz, 1H), 3.76-3.69 (m, 3H), 3.60 (m, 1H), 1.81 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ 88.2, 76.1, 71.8, 67.9, 60.6, 32.3, 23.4.

1. customThe reaction was quenched by addition of sat. aq. Na2SO3
2. additionthen diluted with water
3. extractionThe mixture was extracted with Et2O/EtOAc (1:1)
4. dry with materialThe combined organic phase was dried (Na2SO4)
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customThe residue was purified by flash column chromatography on silica gel

ORD record

ord-e93e5d11d8504b8c9fc45b01e022ae4e

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09024038B2