Tin tetrachloride → HCID 121003791, compound

An argon flushed three-necked flask which was cooled by an ice-water bath was charged with 2-(prop-1-en-2-yl)cyclohexanone (0.88 g, 6.38 mmol), acetaldehyde O-methyl oxime (0.56 g, 7.65 mmol), and SnCl4 (1.66 g, 6.38 mmol) in 1,2-dichloroethane (65 ml). The mixture was stirred for 48 hours at room temperature. The completion of reaction was checked by GC analysis of reaction aliquots quenched with a solution of saturated NaHCO3 in water. The reaction mixture was quenched with sat. aqueous NaHCO3 solution (50 mL). The organic phase was separated and the aqueous layer was extracted with MTBE three times. The combined organic layers were washed with brine (30 mL), dried (MgSO4) and evaporated in vacuo. The crude product was purified by distillation under reduced pressure to yield the title product as a colorless liquid (1.13 g, 84%).

1. temperatureAn argon flushed three-necked flask which was cooled by an ice-water bath
2. customThe completion of reaction
3. customwas checked by GC analysis of reaction aliquots
4. customquenched with a solution of saturated NaHCO3 in water
5. customThe reaction mixture was quenched with sat. aqueous NaHCO3 solution (50 mL)
6. customThe organic phase was separated
7. extractionthe aqueous layer was extracted with MTBE three times
8. washThe combined organic layers were washed with brine (30 mL)
9. dry with materialdried (MgSO4)
10. customevaporated in vacuo
11. distillationThe crude product was purified by distillation under reduced pressure

ORD record

ord-81d5deafb28b4ac094fb9a58779f44f1

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371262B2