Sodium hydride → HCID 57561730, compound

Participants

Reaction Steps

A solution of methyl 4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (500 mg, 2.6 mmol) in DMF (3 mL) was added to a cooled (0° C.) suspension of sodium hydride (114 mg, 60% in oil, 2.8 mmol) in DMF (2 mL). After 10 min, 2-(trimethylsilyl)ethoxymethyl chloride (SEM-Cl) (550 μl, 3.1 mmol) was added. The mixture was stirred at rt for 2 h and was then poured into ice-water and extracted with EtOAc. After concentration, methyl 4-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate was obtained as a crude oil (930 mg).

Provenance & Evidence