Triethylamine → HCID 11041390, compound

Temperature

0 °C

After equipping a thoroughly dried 200 ml-volume three-necked flask with a dropping funnel, a calcium chloride tube and a nitrogen inlet tube, the system atmosphere was charged with nitrogen gas. A stirrer bar coated with Teflon™ was then added into the flask together with 50 ml of dry methylene chloride, 5.0 g (43.1 millimoles) of 2-hydroxysuccinic anhydride and 4.79 g (47.4 millimoles) of dry triethylamine, and the mixture was stirred at 0° C. under the nitrogen atmosphere. To this solution there was added, dropwise and over the period of an hour, 4.50 g (43.1 millimoles) of methacryloyl chloride that had been already placed in the dropping funnel, and then the mixture was stirred at room temperature for 2 hours. After confirming consumption of the starting materials by thin-layer chromatography, the reaction solution was transferred to a 300 ml separatory funnel and washed with 100 ml of water and saturated saline in that order. The aqueous phase was then extracted 3 times with methylene chloride. The organic layer was collected and dried over sodium sulfate anhydride. The dried organic layer was filtered with filter paper and the solvent in the filtrate was distilled off under reduced pressure. This yielded a brown oil. The oil was purified by silica gel chromatography to obtain methacryloxysuccinic anhydride as a colorless transparent oil. The yield was 6.75 g (85%).

1. additionthe system atmosphere was charged with nitrogen gas
2. additionTo this solution there was added
3. stirringthe mixture was stirred at room temperature for 2 hours
4. customconsumption of the starting materials by thin-layer chromatography
5. customthe reaction solution was transferred to a 300 ml separatory funnel
6. washwashed with 100 ml of water and saturated saline in that order
7. extractionThe aqueous phase was then extracted 3 times with methylene chloride
8. customThe organic layer was collected
9. dry with materialdried over sodium sulfate anhydride
10. filtrationThe dried organic layer was filtered
11. filtrationwith filter paper
12. distillationthe solvent in the filtrate was distilled off under reduced pressure
13. customThis yielded a brown oil
14. customThe oil was purified by silica gel chromatography

ORD record

ord-371664954c3d476e8e79853baf6d77dd

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06451501B1