Triphenylphosphine → HCID 57791765, compound

Pyridin-4-ol (10 g, 105.15 mmol), (R)-1-methoxypropan-2-ol (9.48 g, 105.15 mmol) and triphenylphosphine (30.3 g, 115.67 mmol) were added to THF (250 mL) and stirred for 10 minutes. To this was slowly added DIAD (22.49 mL, 115.67 mmol) and the reaction was stirred for 1 hour at 25° C. The solvent was evaporated and diethyl ether (100 mL) was added. To this was added a little triphenyl phosphine oxide and the reaction was stirred for 20 minutes to afford a solid, which was discarded. The solvent was evaporated and the pale yellow gum was acidified with 2.0 HCl, extracted with Et2O (1×75 mL) and the aqueous was then basified with solid KOH. This was then extracted with Et2O (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford yellow gum. This was purified by distillation at 0.43 mBar, collecting fractions that distilled at 80° C. to afford the desired material as a colourless oil (15.30 g, 87% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.34 (3H, d), 3.40 (3H, s), 3.50 (1H, dd), 3.58 (1H, dd), 4.68-4.60 (1H, m), 6.82 (2H, d), 8.40 (2H, d); m/z (LC-MS, ESI+), RT=1.28 (M+H 168).

1. stirringthe reaction was stirred for 1 hour at 25° C
2. customThe solvent was evaporated
3. additiondiethyl ether (100 mL) was added
4. additionTo this was added a little triphenyl phosphine oxide
5. stirringthe reaction was stirred for 20 minutes
6. customto afford a solid, which
7. customThe solvent was evaporated
8. extractionextracted with Et2O (1×75 mL)
9. extractionThis was then extracted with Et2O (3×75 mL)
10. dry with materialthe organic layer was dried over MgSO4
11. filtrationfiltered
12. customevaporated
13. customto afford yellow gum
14. distillationThis was purified by distillation at 0.43 mBar
15. customcollecting fractions
16. distillationthat distilled at 80° C.

ORD record

ord-dc2bf8b784464a65bc79ee23234cd1d8

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129380B2