Methyl iodide → HCID 10192771, compound

Participants

Reaction Conditions

Reaction Steps

To the suspension of NaH (3.05 g at 55% in mineral oil, 70 mmol, 1.4 equiv.) in THF (25 ml) was added neat diethyl carbonate (23.6 g, 200 mmol, 4 equiv.) followed by a solution of 3,3-dimethyl-1-indanone (8.0 g, 50 mmol, 1 equiv.) in THF (25 ml). The mixture was heated to 80° C. for 16 h, then cooled to 50° C. and treated with methyl iodide (21.3 g, 150 mmol, 3 equiv.). After 4.5 h further stirring at 50° C. the mixture was cooled to 5° C. and EtOH (20 ml) followed by H2O (20 ml) was introduced. After dilution with MTBE the phases were separated and the organic layer washed twice with brine, then dried over MgSO4. The residue obtained after concentration in a rotary evaporator was subjected to a short path distillation at 0.05 mbar and 90-115° C., followed by a fine distillation at 0.05 mbar, 112-116° C. to yield the product as a colourless oil (6.5 g, 53%).

Provenance & Evidence