Triethylamine → HCID 59949024, compound

Temperature

0 °C

To a solution of (S)-3-cyclohexyl-1,2-propanediol in CH2Cl2 was added triethylamine (6.6 mL), 2,4,6-triisopropylbenzenesulfonyl chloride (11.5 g), and DMAP (0.386 g). After 14 h, the reaction was diluted with ether, chilled to 0° C., filtered through celite and concentrated. The residue was dissolved in ethanol (100 mL), and 1M NaOH was added (32 mL). After 30 min, the reaction was carefully concentrated, diluted with water (100 mL) and extracted into ether (3×50 mL). The organic extracts were washed with brine (20 mL), dried (MgSO4), filtered and concentrated to give a colorless aromatic oil which was purified first by passage through a plug of silica gel eluting with 5%EtOAc/hexane, then by bulb-to-bulb distillation under reduced pressure to give a colorless aromatic oil (3.3 g, 75%). 1H NMR (300 MHz, CDCl3) δ0.90-1.09 (m, 2H), 1.10-1.85 (m, 11H), 2.43 (dd, J=5.1, 2.7 Hz, 1H), 2.75 (dd, J=5.1, 4.5 Hz, 1H), 2.94 (m, 1H).

1. filtrationfiltered through celite
2. concentrationconcentrated
3. dissolutionThe residue was dissolved in ethanol (100 mL)
4. addition1M NaOH was added (32 mL)
5. waitAfter 30 min
6. concentrationthe reaction was carefully concentrated
7. additiondiluted with water (100 mL)
8. extractionextracted into ether (3×50 mL)
9. washThe organic extracts were washed with brine (20 mL)
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated
13. customto give a colorless aromatic oil which
14. customwas purified first by passage through a plug of silica gel eluting with 5%EtOAc/hexane
15. distillationby bulb-to-bulb distillation under reduced pressure

ORD record

ord-df74e7799f3a4d219e6192d43dcc1264

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06204293B1