Tetrahydrofuran → HCID 58409924, compound

HRID 1844887Notes

Reaction equation

HRID 1844887 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2O[C:12](=O)[C:11]([C:15]#[N:16])=[C:10]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:24]1[CH2:28]O[CH2:26][CH2:25]1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:4]3[C:3]4[C:25](=[CH:24][CH:28]=[CH:7][CH:2]=4)[CH2:26][C:12]=3[C:11]([C:15]#[N:16])=[C:10]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 11243533HCID 11243533, compound

Product 1

HCID 58409924HCID 58409924, compound

Procedure

A mixture of 6-(4-chlorophenyl)-2-oxo-4-(pyrrolidin-1-yl)-2H-pyran-3-carbonitrile (300 mg), indanone-2 (132 mg) and NaH (33 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 197-199° C.; FAB MS 370 (M+); IR (KBr) 2217 cm−1 (CN).

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-9af3143bb31648079cb7b9140fc59946
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

Loading…