Diethyl Ether → HCID 68032719, compound

To a 0° C. solution of butenyl magnesium chloride (45.6 mL, 0.5 M) was added copper(I) chloride (0.113 g) followed by methylcyclopropane oxide (1.12 g) in diethyl ether (5 ml). The reaction mixture was warmed to room temperature and stirred for 20 hours. The mixture was cooled back to 0° C. before pouring into a saturated solution of ammonium chloride (at 0° C.). The mixture was extracted with ethyl acetate (3×). The combined organic fractions were dried over magnesium sulfate, filtered and concentrated carefully. The residue was purified by flash chromatography (ISCO, 0 to 30% ethyl acetate in hexanes) to give the desired product (1.3 g). 1H NMR (400 MHz, CDCl3): δ (ppm) 5.86-5.79 (m, 1H), 5.05-4.99 (m, 1H), 4.97-4.93 (m, 1H), 2.20-2.09 (m, 1H), 2.02-1.92 (m, 2H), 1.73-1.50 (m, 7H), 1.31-1.10 (m, 5H).

1. temperatureThe mixture was cooled back to 0° C.
2. extractionThe mixture was extracted with ethyl acetate (3×)
3. dry with materialThe combined organic fractions were dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated carefully
6. customThe residue was purified by flash chromatography (ISCO, 0 to 30% ethyl acetate in hexanes)

ORD record

ord-c2e23f2164164277b63e6fd2a2ac1aa1

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328138B2