2-Methoxyethanol → HCID 18329731, compound

Triphenylphosphine (2.8 g, 10.7 mmol) was added to an ice-cold solution of 4-iodophenol (2.2 g, 10.0 mmol) and 2-methoxyethanol (0.79 ml, 10.0 mmol) in tetrahydrofuran (10 ml). A solution of diethyl azodicarboxylate (1.88 ml, 11.5 mmol) in tetrahydrofuran (10 ml) was then added dropwise, and the reaction stirred at room temperature for 18 hours. The mixture was evaporated under reduced pressure, the residue partitioned between dichloromethane and hydrochloric acid (2N) and the phases separated. The organic layer was washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with diethyl ether, the resulting suspension filtered and the filtrate concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using pentane:dichloromethane (75:25) as eluant to give the title compound, (2.0 g, 71%) as an oil.

1. customThe mixture was evaporated under reduced pressure
2. customthe residue partitioned between dichloromethane and hydrochloric acid (2N)
3. customthe phases separated
4. washThe organic layer was washed with brine
5. dry with materialdried (MgSO4)
6. customevaporated under reduced pressure
7. customThe residue was triturated with diethyl ether
8. filtrationthe resulting suspension filtered
9. concentrationthe filtrate concentrated under reduced pressure
10. customThe crude product was purified by column chromatography on silica gel

ORD record

ord-1f18bf50c0644ece86466f98334120c5

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06333330B1