Cyclohexene oxide → HCID 16738222, compound

Temperature

80 °C

A mixture of 1e (23.5 g, no more than 182 mmol), cyclohexene oxide (23 mL, 220 mmol) and water (8 mL) was heated at 80° C. for 2 h. The reaction mixture was then partitioned between 40% NaOH aq (60 mL) and Et2O (120 mL). The basic aqueous layer was extracted twice more with Et2O (2×120 mL). The combined organic extracts were dried and concentrated in vacuo. The residue was then heated under high vacuum at 50° C. for 1 h with stirring (to remove the excess of cyclohexene oxide) to yield 32.8 g of 2e (79% yield); as illustrated in FIG. 2. Rf 0.33 (EtOAc-iPrNrH2, 98:2,v/v); 13C NMR (50 MHz, APT, CDCl3) δ 115.5 (+), 70.0 (−), 65.0 (−), 64.5 (+), 57.0 (+), 46.5 (+), 36.0 (+), 33.5 (+), 25.0 (+), 24.0 (+), 21.5 (+); IR (film) 3457 cm−1.

1. customThe reaction mixture was then partitioned between 40% NaOH aq (60 mL) and Et2O (120 mL)
2. extractionThe basic aqueous layer was extracted twice more with Et2O (2×120 mL)
3. customThe combined organic extracts were dried
4. concentrationconcentrated in vacuo
5. temperatureThe residue was then heated under high vacuum at 50° C. for 1 h
6. customto remove the excess of cyclohexene oxide)

ORD record

ord-f83329d2718c4a46b2be25b0ac25f397

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07345087B2