Triphenylphosphine → HCID 178459243, compound

A mixture of 1.994 grams (11.57 mmol) of trans-p-menthane-7,8diol (for preparation, see: Ohloff, G.; Giersch, W. Helv. Chim. Acta., 1980, 63, 76), 3.035 grams (11.57 mmol) of triphenylphosphine, and 20 mL of benzene was chilled in an ice bath and treated portionwise with 2.060 grams (11.57 mmol) of N-bromosuccinimide. The ice bath was removed and the mixture was stirred for 16 hours at room temperature. The mixture was diluted with 50 mL of hexane and the solids were removed by filtering sequentially through celite and filter paper. The filtrate was washed with 0.5 Na2S2O3 solution (2×100 mL), 1 N sodium hydroxide solution (1×50 mL), brine (1×50 mL), dried (Na2SO4), and evaporated. The residue was diluted with hexane and filtered to remove triphenylphospineoxide. The residue was purified by flash chromatography using a 10-50% EtOAc-hexane eluant to give 3.382 grams (88%) of the title compound an oil. 1H NMR (CDCl3) d 0.93-1.28 (6H, m), 1.15 (6H, s), 1.58 (1H, br s), 1.83-2.00 (4H, m), 3.27 (2H, d, J=7 Hz).

1. temperaturewas chilled in an ice bath
2. customThe ice bath was removed
3. additionThe mixture was diluted with 50 mL of hexane
4. customthe solids were removed
5. filtrationby filtering sequentially through celite
6. filtrationfilter paper
7. washThe filtrate was washed with 0.5 Na2S2O3 solution (2×100 mL), 1 N sodium hydroxide solution (1×50 mL), brine (1×50 mL)
8. dry with materialdried (Na2SO4)
9. customevaporated
10. additionThe residue was diluted with hexane
11. filtrationfiltered
12. customto remove triphenylphospineoxide
13. customThe residue was purified by flash chromatography

ORD record

ord-c537a9ed5f8544579f8a6585b4584a36

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174895B1