Ethyl bromoacetate → HCID 59771764, compound

To a solution of 2-(1-azido-ethoxy)-ethanol (0.15 g, 1.14 mmol) in dry tetrahydrofuran (THF) (5 ml) was added NaH (60% dispersion, 0.08 g, 2 mmol) at 0° C. After 15 minutes, ethyl-2-bromoacetate (0.222 ml, 2 mmol) was added. The reaction was maintained at this temperature for 15 minutes and then warmed up to room temperature. The reaction was quenched by addition of saturated aqueous NaHCO3 (5 ml) after 1 hr. After a further period of 5 min, the mixture was partitioned between DCM (50 ml) and saturated aqueous NaHCO3 (50 ml). The aqueous layer was further extracted with DCM (50 ml). All the DCM extracts were combined, dried over MgSO4 and evaporated under reduced pressure. The title compound was obtained as an oil (0.162 g, 65.5%).

1. temperatureThe reaction was maintained at this temperature for 15 minutes
2. customThe reaction was quenched by addition of saturated aqueous NaHCO3 (5 ml) after 1 hr
3. waitAfter a further period of 5 min
4. customthe mixture was partitioned between DCM (50 ml) and saturated aqueous NaHCO3 (50 ml)
5. extractionThe aqueous layer was further extracted with DCM (50 ml)
6. dry with materialdried over MgSO4
7. customevaporated under reduced pressure

ORD record

ord-f57bbae9b86c476994e76d169d98300f

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07414116B2