Water → HCID 12509450, compound

Participants

Reaction Steps

Titanium tetrachloride (0.1 dm3, 0.9 mole) in carbon tetrachloride (0.1 dm3) was added to stirred tetrahydrofuran (0.25 dm3) at 0° over 5 minutes. To the yellow solution a premix of 1,4-dichloro-3-buten-2-one (0.0556 kg, 0.4 mole) and dimethyl malonate (0.0528 kg, 0.4 mole) in tetrahydrofuran (0.2 dm3) was added dropwise over 10 minutes maintaining the temperature at 0°. A solution of pyridine (0.13 dm3, 1.6 moles) in tetrahydrofuran (0.1 dm3) was added to the above brown mixture dropwise over 30 minutes at 0° and the resultant mixture stirred at ambient temperature for three hours and then treated with water (1 dm3). The mixture was separated, the aqueous phase re-extracted with dichloromethane (2×0.25 dm3) and the combined organic extract washed with brine (2×0.1 dm3) and then dried over magnesium sulphate (0.10 kg). Filtration and evaporation of the filtrate under reduced pressure gave a red oil which crystallised on standing. Yield 0.064 kg (63.3%), m.p. 56°.

Provenance & Evidence