Tetrahydrofuran → HCID 131723132, compound

Temperature

0 °C

To a 300-mL three-necked round-bottom flask fitted with nitrogen inlet, magnetic stirrer, and a dropping funnel, 8.7 g (0.05 mol) of 2,7-dimethyl-2,7-octanediol prepared as in Background Example 1, 16.7 mL (0.12 mol) of triethylamine (Fisher), 1.46 g (0.012 mol) of 4-(dimethylamino) pyridine (Aldrich), and 80 ml of dry THF were added under nitrogen atmosphere, and the solution was cooled to 0° C. The mixture of 10.8 g (0.12 mol) of distilled acryloyl chloride (Aldrich) and 20 mL of dry THF was added dropwise. After 2 hours of stirring, the reaction vessel was allowed to warm to room temperature and stirring was continued overnight. Precipitated salts were removed by filtration. A 150 mL volume of diethyl ether was added to the filtrate, and the resulting precipitate was also removed by filtration. The reaction mixture was washed with distilled water and dilute aqueous sodium bicarbonate and was dried with anhydrous magnesium sulfate. Evaporation of the solvents gave an oily residue, which was then purified by column chromatography (silica gel/hexanes). A colorless oily liquid was obtained, yield 3.2 g (23%). 1HNMR(CDCl3), δ from TMS: 1.29 [m, 4H —CH2CH2C(CH3)2O—], 1.42 [s, 12H, —C(CH3)2O—], 1.74 [m, 4H, —CH2CH2C(CH3)2O—], 5.66, 6.25 [m, 4H, CH2═CH—]. 5.98 [m, 2H, CH2═CH—]. IR (film): 2978, 2943, 2868 cm−1(C—H stretch); 1722 cm−1(C═O stretch); 1636, 1620 cm−1(C═C stretch); 1299, 1205 cm−1(C—O—C stretch); 985 cm−1(═CH wag); 964 cm−1(═CH2 wag); 812 c−1(═CH2 twist).

1. customTo a 300-mL three-necked round-bottom flask fitted with nitrogen inlet, magnetic stirrer, and a dropping funnel
2. additionwere added under nitrogen atmosphere
3. additionwas added dropwise
4. temperatureto warm to room temperature
5. stirringstirring
6. waitwas continued overnight
7. customPrecipitated salts were removed by filtration
8. additionA 150 mL volume of diethyl ether was added to the filtrate
9. customthe resulting precipitate was also removed by filtration
10. washThe reaction mixture was washed with distilled water and dilute aqueous sodium bicarbonate
11. dry with materialwas dried with anhydrous magnesium sulfate
12. customEvaporation of the solvents
13. customgave an oily residue, which
14. customwas then purified by column chromatography (silica gel/hexanes)
15. customA colorless oily liquid was obtained

ORD record

ord-e0241fc8b1054b43a9a00832c8facec8

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06355702B1