3-Chloro-2-methyl-1-propene → HCID 58738316, compound

Temperature

50 °C

To a solution of L-leucinol (20.0 g, 0.17 mol) in an anhydrous THF (200 mL) was portionwise added 60% NaH (7.92 g, 0.198 mol). The resulting mixture was stirred for 30 min. at room temperature and further for 2 hours at 50° C. The mixture was then cooled to room temperature. To the resulting suspension was dropwise added a solution of 3-chloro-2-methylpropene (15.45 g, 0.17 mol) in an anhydrous THF (50 mL). The resulting mixture was stirred for 20 hours at room temperature. The THF was distilled off under reduced pressure. To the residue were successively added a mixture of ice and water and diethyl ether. The mixture was stirred for 5 min. at room temperature, and the organic portion was separated. The aqueous portion was subjected to extraction with diethyl ether. The extract was combined with the organic portion. The combined organic portion was washed with 1 mol/L aqueous hydrochloric acid (7 mL) and subjected to extraction with 1 mol/L aqueous hydrochloric acid (153 mL). The resulting hydrochloric acid extract was made to approx. pH 10 by addition of potassium carbonate and subjected to extraction with diethyl ether. The organic portion was washed with water, dried over sodium sulfate, and placed under reduced pressure to distill the solvent off. There was obtained the titled compound (20.22 g, 69.2%) as an oily product.

1. temperatureThe mixture was then cooled to room temperature
2. stirringThe resulting mixture was stirred for 20 hours at room temperature
3. distillationThe THF was distilled off under reduced pressure
4. additionTo the residue were successively added
5. additiona mixture of ice and water and diethyl ether
6. stirringThe mixture was stirred for 5 min. at room temperature
7. customthe organic portion was separated
8. extractionThe aqueous portion was subjected to extraction with diethyl ether
9. washThe combined organic portion was washed with 1 mol/L aqueous hydrochloric acid (7 mL)
10. extractionsubjected to extraction with 1 mol/L aqueous hydrochloric acid (153 mL)
11. extractionThe resulting hydrochloric acid extract
12. additionwas made to approx. pH 10 by addition of potassium carbonate
13. extractionsubjected to extraction with diethyl ether
14. washThe organic portion was washed with water
15. dry with materialdried over sodium sulfate
16. distillationto distill the solvent off

ORD record

ord-0f7ed07a9c3440a29fe745854b3b6944

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07132573B2