Chloroacetaldehyde → HCID 54283362, compound

A solution of titanium (IV) chloride (11 ml, 0.1M) in carbon tetrachloride (25 ml) was added dropwise to anhydrous tetrahydrofuran (200 ml) at 0° under nitrogen. On completion of the addition, diethyl malonate (7.6 ml, 50 mM) and anhydrous chloroacetaldehyde (5 g, 63 mM) were added, then a solution of pyridine (16 ml, 0.2M) in anhydrous tetrahydrofuan (35 ml) was added dropwise over 2 hours at 0°. On completion of the addition, the dark mixture was allowed to warm to room temperature, stirred at this temperature for 2 hours, then heated under reflux overnight. The reaction mixture was cooled, water (500 ml) added and the mixture extracted with diethyl ether (2×250 ml). The combined extracts were washed with water (500 ml), saturated sodium bicarbonate solution (500 ml) and brine (500 ml), dried (MgSO4) and evaporated to give a brown oil. Column chromatography of this oil on silica (eluent 1:1 hexane:dichloromethane) afforded the title compound as a pale yellow oil 4.9 g, 44%.

1. additionwere added
2. additionOn completion of the addition
3. temperatureheated
4. temperatureunder reflux overnight
5. temperatureThe reaction mixture was cooled
6. extractionthe mixture extracted with diethyl ether (2×250 ml)
7. washThe combined extracts were washed with water (500 ml), saturated sodium bicarbonate solution (500 ml) and brine (500 ml)
8. dry with materialdried (MgSO4)
9. customevaporated
10. customto give a brown oil

ORD record

ord-03eb7fe84a754667b342ed7996b108c3

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05220024