Tetrahydrofuran → HCID 58409954, compound

HRID 1844888Notes

Reaction equation

HRID 1844888 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

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 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).

Workup

  1. customAfter completion, the reaction solvent was evaporated under vacuum to dryness
  2. customcrude solid was quenched with ice water
  3. customfinally purified by column chromatography

Sources & evidence

ORD record
ord-03f9f089f31649c79cecdf45b4df6d93
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

Loading…