Phenylsilane → HCID 54589870, 화합물

온도

-15 °C

Tris(2,2,6,6-tetramethyl-3,5-heptanedionato)manganese(III) (281 mg, 0.460 mmol) was dissolved in 2-propanol (100 mL) in a 1 L 3-necked flask equipped with addition funnel, gas inlet, and thermometer. The solution was cooled to −15° C. under nitrogen. Di-tert-butyl azodicarboxylate (8.11 g, 34.5 mmol) and phenylsilane (2.9 mL, 23 mmol) were dissolved in dichloromethane (100 mL) and this resulting orange solution was added to the above cooled solution dropwise over 10 minutes, maintaining the internal temperature at approximately −10° C. A solution of [1.1.1]propellane (Journal of the American Chemical Society (2001), 123(15), 3484-3492) (50 mL, 23 mmol, 0.46 M in pentane) was added to the reaction mixture in one portion at −15° C. The reaction was stirred at −15° C. for 30 minutes. The cold bath was removed and the reaction was allowed to warm to room temperature and stir for 4 hours. The reaction was concentrated and purification by flash column chromatography (5-20% ethyl acetate/heptanes) gave the title compound (6.38 g, 93%) as a clear oil which solidified upon standing. −ESI (M−H) 297.4; 1H NMR (400 MHz, CDCl3, δ): 6.26 (br. s., 1H), 2.37 (s, 1H), 2.02 (s, 6H), 1.45 (s, 18H).

1. customequipped with addition funnel, gas inlet
2. additionthis resulting orange solution was added to the above cooled solution dropwise over 10 minutes
3. temperaturemaintaining the internal temperature at approximately −10° C
4. customThe cold bath was removed
5. temperatureto warm to room temperature
6. stirringstir for 4 hours
7. concentrationThe reaction was concentrated
8. custompurification by flash column chromatography (5-20% ethyl acetate/heptanes)

ORD 기록

ord-a7d23fe1668443da9816c1e7b2db0903

출처 데이터셋

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08802688B2