Hydrogen Peroxide → 2,3-dihydro-1H-indene-1,4-diyldimethanol

Participants

Reaction Steps

To a solution of methyl 1-methylidene-2,3-dihydro-1H-indene-4-carboxylate (1.4 g, 7.4 mmol) in THF (15 mL) was added borane THF complex (1.0 M, 9.7 mL, 9.7 mmol) at 0° C. The mixture was allowed to stir for 3 hours. To the reaction was added 2N sodium hydroxide (7.5 mL, 15 mmol) and 30% hydrogen peroxide (1.7 mL, 15 mmol). The mixture was then allowed to warm to RT. LC analysis showed complete reaction within 30 minutes. The reaction was neutralized with NH4Cl, diluted with water, extracted with EtOAc, dried over sodium sulfate, and purified by silica gel chromatography. The intermediate hydroxyester (1.1 g) was collected after removal of solvents. To a DCM (10 mL) solution of the hydroxyester (750 mg, 3.6 mmol) was added DIBAL-H (18 mL, 18 mmol) at −78° C. The reaction was allowed to stir for 16 h, warming to RT slowly. The reaction was diluted with DCM (30 mL), and worked up with Roschelle's salt. The organic layer was separated using a separatory funnel, dried over sodium sulfate, and the crude product was purified by silica gel chromatography to afford 2,3-dihydro-1H-indene-1,4-diyldimethanol. 1H-NMR (500 MHz, CDCl3) δ ppm 7.25-7.30 (m, 3H), 4.72 (s, 3H), 3.85 (m, 2H), 3.42 (m, 1H), 3.03 (m, 1H), 2.95 (m, 1H), 2.34 (m, 1H), 2.04 (m, 1H).

Provenance & Evidence