Water → HCID 54298403, compound

Methyl glyoxalate (8.80 g, 0.1 mol, 1.0 eq) and 1-hexene (16.80 g, 0.2 mol, 2.0 eq) are dissolved in dry dichloromethane (150 ml, freshly distilled from calcium hydride) under a nitrogen atmosphere. Stannic chloride (3.51 ml, 0.03 mol, 0.3 eq) is added dropwise with stirring and cooling at 0° C. (ice/water bath). After half an hour the reaction mixture is allowed to warm to room temperature and stirred for a further 21 hours before being neutralised with triethylamine (4.2 ml, 0.03 mol, 0.3 eq) with a further 5 minutes stirring. Water (50 ml) and dichloromethane (100 ml) are added, the organic layer is separated, washed in turn with water (50 ml) and brine (50 ml), dried over anhydrous magnesium sulphate and evaporated. The crude oil is purified by short path distillation (b p 120-130° C./0.7 mm Hg) to furnish the ester product (23) as a colourless liquid, 11.49 g (67% yield).

1. distillationfreshly distilled from calcium hydride) under a nitrogen atmosphere
2. waitAfter half an hour the reaction mixture is allowed
3. stirringstirred for a further 21 hours
4. stirringstirring
5. customthe organic layer is separated
6. washwashed in turn with water (50 ml) and brine (50 ml)
7. dry with materialdried over anhydrous magnesium sulphate
8. customevaporated
9. distillationThe crude oil is purified by short path distillation (b p 120-130° C./0.7 mm Hg)

ORD record

ord-c83b69ea743b44d0a8d19edb3201f974

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05108751