Chloride → HCID 25193228, compound

To a solution of (4-aminophenyl)methanol 32 (0.31 g, 2.50 mmol) in anhydrous pyridine (8 mL) was added chlorotrimethylsilane (0.32 mL, 2.50 mmol) at room temperature and stirring continued for 2 h. The mixture, together with a catalytic amount of DMAP, was added to a mixture of crude chloride 31 (obtained as described above) in pyridine at 0° C. The reaction was allowed to warm to room temperature and stirring continued overnight. Water (5 mL) and 1 M TBAF in tetrahydrofuran (THF) (0.25 mL, 0.25 mmol) were added and stirring continued for additional 30 min. EtOAc (50 mL) and 1N HCl (30 mL) were added, the two layers were separated, the organic layer was washed with 1N HCl (30 mL) and saturated brine (30 mL) and dried over Na2SO4. Solvent was evaporated off and the crude was purified by preparative TLC, eluting with acetone/hexanes 1:1 to give compound 33 (195 mg, 30%) as yellow-white solid. 1H-NMR (CDCl3, 400 MHz) δ 1.24 (4H, m), 1.49-1.59 (4H, m), 2.17-2.25 (4H, m), 3.58 (3H, s), 4.50 (2H, s), 7.13 (2H, d, J=8.4 Hz), 7.37 (2H, d, J=8.4 Hz).

1. stirringstirring continued overnight
2. stirringstirring
3. waitcontinued for additional 30 min
4. customthe two layers were separated
5. washthe organic layer was washed with 1N HCl (30 mL) and saturated brine (30 mL)
6. dry with materialdried over Na2SO4
7. customSolvent was evaporated off
8. customthe crude was purified by preparative TLC
9. washeluting with acetone/hexanes 1:1

ORD record

ord-6bea3af042084881b38cf20869cc2edd

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188054B2