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

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).

1. customreaction within 30 minutes
2. extractionextracted with EtOAc
3. dry with materialdried over sodium sulfate
4. custompurified by silica gel chromatography
5. customThe intermediate hydroxyester (1.1 g) was collected
6. customafter removal of solvents
7. stirringto stir for 16 h
8. temperaturewarming to RT slowly
9. customThe organic layer was separated
10. dry with materialdried over sodium sulfate
11. customthe crude product was purified by silica gel chromatography

ORD record

ord-329c1d9c55334751b3d0c3423d625134

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056859B2