Diethyl Ether → HCID 58568010, compound

A Grignard solution of 2-ethylhexylmagnesium-bromide in diethylether (1.0 M, 1.96 mL, 1.96 mmol) was slowly added via syringe to a stirred mixture of pyridin-2-yl undec-10-enethioate (0.54 g, 1.96 mmol) in THF (50 mL) at 0° C. under N2 atmosphere. After vigorously stirring for another 30 minutes, the reaction was completed by adding (2.0 M, 50 mL). The organic phase was separated and the aqueous phase was extracted with diethylether. The combined organic phases were washed with a saturated bicarbonate solution and brine, dried over MgSO4 and evaporated under reduced pressure to give a yellow oil. The resulting oil was purified by vacuum distillation at 90-100° C. at 10−2 mbar. 1H-NMR (CDCl3): δ=5.85-5.67 (m, 1H), 5.00-4.83 (m, 2H), 2.37-2.22 (m, 4H), 1.99 (q, J=14.0 Hz, J=6.9 Hz, 2H), 1.89-1.76 (m, 1H), 1.61-1.44 (m; 4H), 1.39-1.09 (m, 16H), 0.90-0.74 (m, 6H).

1. additionby adding (2.0 M, 50 mL)
2. customThe organic phase was separated
3. extractionthe aqueous phase was extracted with diethylether
4. washThe combined organic phases were washed with a saturated bicarbonate solution and brine
5. dry with materialdried over MgSO4
6. customevaporated under reduced pressure
7. customto give a yellow oil
8. distillationThe resulting oil was purified by vacuum distillation at 90-100° C. at 10−2 mbar

ORD record

ord-76e96e9385b5434ea74a64eab4fdc059

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329923B2