Hydrogen Peroxide → HCID 67745285, compound

Temperature

25 °C

A solution of 1,4-cyclohexanedione monoethylene ketal (9.37 g, 60 mmol) in THF (50 mL) was added to a suspension of KH (2.57 g, 63 mmol) in THF (200 mL) at rt under argon. After being stirred at rt (25° C.) for 30 min, the mixture was cooled to 0° C., and triethylborane (75 mL of 1M solution in THF) was added. The mixture was stirred for 30 min prior to the introduction of allyl bromide (7.8 mL, 90 mmol). After 1 h, H2O2 (30%, 50 mL) and NaOH (3M, 50 mL) were added at 0° C., and stirring was continued for 30 min at rt prior to removal of THF by rotary evaporation. The aqueous residue was extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated. Flash chromatography (30% ethyl acetate in hexanes) gave 10.1 g (86%) of 2 as an oil: IR (neat) 2957, 2887, 1714, 1438, 1140, 1049 cm-1 ; 1H NMR δ5.72 (m, 1H), 5.02 (m, 2H), 4.01 (m, 4H), 2.65 (m, 3H), 2.46 (m, 1H), 2.05 (m, 4H); 13C NMR δ210.6, 135.7, 116.6, 107.3, 64.6, 64.4, 45.7, 39.8, 38.0, 34.4, 33.1; MS m/z 196 (M30 ), 168, 155, 99.

1. temperaturethe mixture was cooled to 0° C.
2. stirringThe mixture was stirred for 30 min
3. waitAfter 1 h
4. stirringstirring
5. waitwas continued for 30 min at rt
6. customto removal of THF
7. customby rotary evaporation
8. extractionThe aqueous residue was extracted with ethyl acetate
9. washwashed with brine
10. dry with materialdried over MgSO4
11. concentrationconcentrated

ORD record

ord-bcdf389d47964b0cbf96e9bc06e5f273

Source dataset

uspto-grants-1996_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05547960