Triphenylphosphine → HCID 57791810, compound

Temperature

20 °C

Di-tert-butyl azodicarboxylate (719 mg, 3.12 mmol) was added in one portion to pyridin-4-ol (YY) (297 mg, 3.12 mmol), 1,3-difluoropropan-2-ol (100 mg, 1.04 mmol) and Polymer supported triphenylphosphine (1.89 mmol/g; 1016 mg, 3.12 mmol) in dichloromethane (10 mL) at 20° C. under air. The resulting suspension was stirred at 20° C. for 4 hours. The mixture was filtered and the solvent evaporated to a yellow oil. The reaction mixture was diluted with dichloromethane (25 mL), and washed sequentially with 2M NaOH (2×10 mL) and saturated brine (10 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. This was re-dissolved in dichloromethane (25 mL), and washed with 2M HCl (10 mL). The aqueous layer was basified with 2M NaOH and extracted with dichloromethane (×3). The combined organic layers were dried over MgSO4, filtered and evaporated to afford the desired compound as a viscous oil (90 mg, 50%); 1H NMR (400.132 MHz, CDCl3) δ 4.60-4.67 (2H, m), 4.71-4.76 (2H, m), 4.78-4.90 (1H, m), 6.92 (2H, d), 8.48 (2H, d); m/z (LC-MS, ESI+), RT=1.53 (M+H 174).

1. customat 20° C.
2. filtrationThe mixture was filtered
3. customthe solvent evaporated to a yellow oil
4. additionThe reaction mixture was diluted with dichloromethane (25 mL)
5. washwashed sequentially with 2M NaOH (2×10 mL) and saturated brine (10 mL)
6. dry with materialThe organic layer was dried over MgSO4
7. filtrationfiltered
8. customevaporated
9. customto afford crude product
10. washwashed with 2M HCl (10 mL)
11. extractionextracted with dichloromethane (×3)
12. dry with materialThe combined organic layers were dried over MgSO4
13. filtrationfiltered
14. customevaporated

ORD record

ord-347759c7bb844a6bb18412fad175d3d4

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129380B2