Water → 2-Methyl-2-(1-oxo-2,3-dihydro-1H-inden-5-yl)propanenitrile

Participants

Reaction Conditions

Reaction Steps

2-Methyl-2-(3-trimethylsilanylethynylphenyl)-propionitrile (4.00 g, 16.6 mmol) was added to a mixture of THF (35 mL), TEA (4.82 mL, 34.6 mmol), water (3.12 mL, 173 mmol), [Rh(COD)Cl]2 (83 mg, 168 μmol) and triphenylphosphine (1.81 g, 6.90 mmol) in a stainless steel autoclave. The reactor was sealed and flushed with carbon monoxide, and then it was pressurized with carbon monoxide (500 psi). The stirred mixture was heated at 160° C. for 4 hours. After cooling to ambient temperature, the reaction mixture was concentrated to a black residue and chromatographed on silica gel with 20-40% ethyl acetate in hexane. Obtained 2-methyl-2-(1-oxo-indan-5-yl)-propionitrile (2.71 g, 82%) as a brown solid. MS (DCI/NH3) m/z: 200.0 [M+H]+. 1H NMR (DMSO-d6) δ: 1.73 (s, 6H), 2.65 (m, 2H), 3.14 (m, 2H), 7.60 (dd, 1H), 7.68 (d, 1H), 7.74 (d, 1H).

Provenance & Evidence