Tetrahydrofuran → HCID 58409954, compound

Reaction equation

O=[C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:5]=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)O1.[H-].[Na+].[CH2:24]1[CH2:28]O[CH2:26][CH2:25]1>>[N:10]1([C:6]2[CH:5]=[C:4]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[C:6]3[C:5]4[C:25](=[CH:24][CH:28]=[CH:15][CH:4]=4)[CH2:26][C:2]=3[C:7]=2[C:8]#[N:9])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

HCID 673948316-(4-Methylphenyl)-2-oxo-4-(pyrrolidin-1-yl)-2H-pyran-3-carbonitrile

Product 1

HCID 58409954HCID 58409954, compound

Procedure

A mixture of 2-oxo-4-(pyrrolidin-1-yl)-6-p-tolyl-2H-pyran-3-carbonitrile (280 mg), indanone-2 (132 mg) and NaH (39 mg) in THF was stirred for <5 min. After completion, the reaction solvent was evaporated under vacuum to dryness and crude solid was quenched with ice water and subsequently neutralized with dil. HCl, finally purified by column chromatography using ethylacetate-hexane as eluent. White solid; mp 182-184° C.; ESMS 351 (M++1); IR (KBr) 2205 cm−1 (CN); 1H NMR (200 MHz, CDCl3) δ 1.99-2.06 (m, 4H, 2CH2), 2.48 (s, 3H, CH3), 3.63-3.72 (m, 4H, 2CH2) δ 4.03 (s, 2H, CH2), 6.45 (s, 1H, ArH), 6.80 (d, J=7.6 Hz, 1H, ArH), 7.03-7.18 (m, 2H, ArH), 7.27-7.36 (m, 4H, ArH), 7.47 (d, J=7.0 Hz, 1H, ArH).