Tetrahydrofuran → HCID 86684753, compound

Temperature

0 °C

In a flask containing a solution of 2 (1.0 g, 5.81 mmol) in THF (7.2 mL) was added H2O (3.5 mL). The mixture was cooled with an ice bath and then N-methylmorpholine N-oxide (1.0 g, 8.71 mmol) was added followed by osmium tetroxide (0.074 g, 0.291 mmol) and the mixture stirred at 0° C. for 1 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL×2). The organic layer was separated, washed with brine, concentrated, and chromatographed on silica gel eluted with ethyl acetate/hexanes (0-20%) to afford 0.66 g (55%) of 41 as an oil. 1HNMR (CDCl3) δ 1.92 (1 H, t, J=5.0 Hz), 2.36 (1 H, d, J=5.0 Hz), 2.80 (2 H, m), 3.52 (1 H, m), 3.73 (1 H, m), 3.93 (1 H, m), 7.46 (1 H, d, J=11.0 Hz), 8.10 (1 H, s); LC/MS (M+1) 207.

1. temperatureThe mixture was cooled with an ice bath
2. extractionextracted with ethyl acetate (50 mL×2)
3. customThe organic layer was separated
4. washwashed with brine
5. concentrationconcentrated
6. customchromatographed on silica gel
7. washeluted with ethyl acetate/hexanes (0-20%)

ORD record

ord-0a1a2f014c414fc09e21c0b5e32a33c7

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921373B2