Malonate Ion → 2-(2-Bromoallyl)propane-1,3-diol

Temperature

-78 °C

Lithium aluminum hydride (1.9 g, 7.65 mmol) was slurried in anhydrous diethyl ether (50 ml) and cooled to −78° C. in a dry ice/acetone bath. A solution of the product from step A (0.639 g, 16.84 mmol) in dry ether (26 ml) was then added dropwise. After the malonate was added, the solution was allowed warm to room temperature and stirring was continued for 3 hours. The reaction was quenched with brine (50 ml), extracted with ethyl acetate (3×25 ml) and dried over MgSO4. The solvent was removed in vacuo to give the desired product (1.3 g, 86%) which was used for the next step without further purification. 1H-NMR (300 MHz, CDCl3) δ 5.66 (d, J=1.2 Hz, 1H), 5.48 (d, J=1.5 Hz, 1H), 3.86 (m, 2H), 3.73 (m, 2H), 2.51 (d, J=7.5 Hz, 2H), 2.40 (br s, 2H), 2.15 (m, 1H).

1. temperaturethe solution was allowed warm to room temperature
2. customThe reaction was quenched with brine (50 ml)
3. extractionextracted with ethyl acetate (3×25 ml)
4. dry with materialdried over MgSO4
5. customThe solvent was removed in vacuo

ORD record

ord-844490d6fa82408aba83a20f32af5100

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08648116B2