Triethylamine → 2-Methyl-2-vinyl-1-tetralone

An oven dried Schlenk tube equipped with a rubber septum was purged with argon. The septum was removed, and the tube was charged with palladium acetate (5.6 mg, 0.025 mmol, 5 mol %) and (−)-2-(dicyclohexylphosphino)-2′-(dimethylamino)-1,1′-binaphthyl (13.6 mg, 0.028 mmol 5.5 mol %). The tube was capped with the septum, purged with argon, and toluene (2 mL) and triethylamine (5 mg, 0.05 mmol) were added through the septum. The mixture was stirred at room temperature for 3 min, then vinyl bromide (1.0 mL 1.0 mmol) and 2-methyl-1-tetralone (81 mg, 0.5 mmol) were added through the septum. The septum was removed and sodium t-butoxide (96 mg, 1.0 mmol) was added. The tube was capped with the septum and purged with argon. Additional toluene (4 mL) was added and the mixture was stirred at room temperature for 2 h. The mixture was quenched with saturated aqueous ammonium chloride (5 mL), diluted with ether (20 mL), and poured into a separatory funnel. The layers were separated and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 83 mg (88%) of title compound. The ee was 9 determined to be 79% by chiral HPLC analysis.

1. customAn oven dried Schlenk tube
2. customequipped with a rubber septum
3. customwas purged with argon
4. customThe septum was removed
5. customThe tube was capped with the septum
6. additionwere added through the septum
7. customThe septum was removed
8. customThe tube was capped with the septum
9. custompurged with argon
10. additionAdditional toluene (4 mL) was added
11. stirringthe mixture was stirred at room temperature for 2 h
12. customThe mixture was quenched with saturated aqueous ammonium chloride (5 mL)
13. additiondiluted with ether (20 mL)
14. additionpoured into a separatory funnel
15. customThe layers were separated
16. extractionthe aqueous layer was extracted with ether (20 mL)
17. washThe combined organic layers were washed with brine (20 mL)
18. dry with materialdried over anhydrous magnesium sulfate
19. filtrationfiltered
20. concentrationconcentrated in vacuo
21. customThe crude material was purified by flash chromatography on silica gel

ORDレコード

ord-bf899a9fdf50424da70d19f94c4a94d2

出典データセット

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06867310B1