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

HRID 656456Notes

Reaction equation

[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[C:13][Si](C)(C)C)[CH:7]=1)([CH3:5])[C:3]#[N:4].[OH2:18].[C:19]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:1][C:2]([C:6]1[CH:7]=[C:8]2[C:9](=[CH:10][CH:11]=1)[C:19](=[O:18])[CH2:13][CH2:12]2)([CH3:5])[C:3]#[N:4]

Participants

Conditions

Temperature: 160 °C

Procedure

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).

Workup

customThe reactor was sealed
customflushed with carbon monoxide
temperatureAfter cooling to ambient temperature
concentrationthe reaction mixture was concentrated to a black residue
customchromatographed on silica gel with 20-40% ethyl acetate in hexane

Sources & evidence

ORD record: ord-fa3845e72dc640f6b0c65894f2db07a2
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071762B2

Reaction notes

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