反应详情

To a suspension of 2-thiophenemethanol (4.15 mL, 43.64 mmol), triphenylphosphine (12.59 g, 48.01 mmol) and N-hydroxyphthalimide (7.83 g, 48.01 mmol) in THF (120 mL) at 0° C. was added dropwise diethylazodicarboxylate (7.56 mL, 48.01 mmol) in THF (20 mL). The reaction mixture was allowed to stir for 15 h after which the solvent was removed under vacuum to dryness. Et2O (50 mL) was added to triturate the triphenylphosphine oxide and diethylhydrazinedicarboxylate, which was filtered off and washed with a little Et2O. The ethereal solution was concentrated under vacuum to give a residue which was filtered through a pad of silica (eluting with EtOAc/PE, 3:7). Removal of the solvent under reduced pressure afforded N-(thiophen-2-ylmethoxy)phthalimide (1.50 g, 13%), as a pale yellow solid.

1. customwas removed under vacuum to dryness
2. additionEt2O (50 mL) was added
3. customto triturate the triphenylphosphine oxide and diethylhydrazinedicarboxylate, which
4. filtrationwas filtered off
5. washwashed with a little Et2O
6. concentrationThe ethereal solution was concentrated under vacuum
7. customto give a residue which
8. filtrationwas filtered through a pad of silica (eluting with EtOAc/PE, 3:7)
9. customRemoval of the solvent under reduced pressure