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

Temperatur

-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-Eintrag

ord-29302142d3da4d53a33eb3470f82bc42

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08829052B2