Ethyl Acetate → (E)-N-(3-Chloro-2-propenyl)-N-propyl-3-hydroxybenzylamine

Temperature

50 °C

To a solution of 3.30 g (20 mmol) of N-propyl-3-hydroxybenzyiamine in 20 ml of dimethyl sulfoxide were added 1.82 g (20 mmol) of 1,3-dichloropropene (E/Z=2/1) and 1.38 g (10 mmol) of ground potassium carbonate under ice cooling. The mixture was stirred for 1.5 hours at room temperature and for 3 hours at 50° C., poured into 70 ml of ethyl acetate, washed with 50 ml×2 of water and 50 ml of saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel chromatography (n-hexane→n-hexane/ethyl acetate=9/1). The desired fractions were put together and concentrated under reduced pressure to obtain 2.29 g (yield: 48%) of the above identified compound as an oil.

1. washwashed with 50 ml×2 of water and 50 ml of saturated sodium chloride aqueous solution
2. dry with materialdried over anhydrous magnesium sulfate
3. concentrationconcentrated under reduced pressure
4. concentrationconcentrated under reduced pressure
5. customto obtain 2.29 g (yield: 48%) of the

ORD record

ord-1aa7636cd8114caba6feb9b41f28c00c

Source dataset

uspto-grants-1994_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05359091