Sodium bis(trimethylsilyl)amide → HCID 392891, Verbindung

Temperatur

0 °C

NaN(TMS)2 (1 mL, 1 mmol) was added to an ice cold suspension of hexyltriphenylphosphonium bromide (0.427 g, 1 mmol) in THF (20 mL) and the solution was stirred for 30 min at 0° C. A solution of the benzophenone 39 (0.2 g, 0.33 mmol) in THF (5 mL) was added to the preformed ylide and the solution was stirred at rt overnight. The mixture was partitioned between 1 N HCl (100 mL) and ethyl acetate (100 mL). The organic layer was evaporated and flash chromatographed on SiO2 (230-400 mesh, 50.0 g), eluting with hexanes-ethyl acetate (5:1). The fractions which contained the product were pooled, evaporated, and chromatographed on silica gel (230-400 mesh, 20 g), eluting with hexanes-ethyl acetate (5:1), to give the product 40 (0.022 g, 9%) as an oil: 1H NMR (CDCl3, 300 MHz) δ 7.69 (s, 2H), 7.54 (d, J=2.0 Hz, 1H), 7.52 (d, J=2 Hz, 1H), 6.01 (t, J=7.6 Hz, 1H), 3.93 (s, 3H), 3.89 (s, 3H), 3.88 (s, 3H), 3.85 (s, 3H), 2.05 (q, J=7.3 Hz, 2H), 1.42 (m, 2H), 1.25 (m, 2H), 0.85 (t, J=6.7 Hz, 3H); IR (neat) 2953, 2929, 1742, 1738, 1731, 1713 cm−1; HRFABMS calcd for C25H28I2O6 m/z 677.9975 (M+). Found: m/z 677.9954. Anal. (C25H28I2O60.5EtOAc), C, H.

1. stirringthe solution was stirred at rt overnight
2. customThe mixture was partitioned between 1 N HCl (100 mL) and ethyl acetate (100 mL)
3. customThe organic layer was evaporated
4. customflash chromatographed on SiO2 (230-400 mesh, 50.0 g)
5. washeluting with hexanes-ethyl acetate (5:1)
6. customevaporated
7. customchromatographed on silica gel (230-400 mesh, 20 g)
8. washeluting with hexanes-ethyl acetate (5:1)

ORD-Eintrag

ord-350efe5fa38247c1a0512957dd14db9e

Quelldatensatz

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06569897B1