Sodium hydride → 1-Cyclopropylidene-6-methoxy-2,3-dihydro-1H-indene

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Reaction Steps

NaH (1.5 g, 62 mmol) was added to a suspension of cyclopropyltriphenyl-phosphonium bromide (24 g, 62 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) in THF (100 mL), and the resulting mixture was stirred at room temperature for 2 hours. Then, 6-methoxy-1-indanone (H10.1) (Oakwood Products, Inc.) (5.00 g, 31 mmol) and tris(2-(2-methoxyethoxy)ethyl)amine (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) (1.1 mL, 3.1 mmol) were added slowly. The resulting mixture was stirred at room temperature for 10 minutes and then at 62° C. for 4 hours. The reaction mixture was concentrated and purified by chromatography (silica gel, eluting with 1:9 EtOAc/hexane) to provide H10.2 (4.53 g, 79% yield) as a solid. MS ESI (pos.) M/E: 187.1 (M+H).

Provenance & Evidence