Tetrahydrofuran → HCID 58409939, compound

HRID 1844886Notes

Reaction equation

HRID 1844886 reaction equation
O=[C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)O1.[H-].[Na+].[CH2:25]1[CH2:29]O[CH2:27][CH2:26]1>>[N:10]1([C:6]2[CH:5]=[C:4]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:6]3[C:5]4[C:26](=[CH:25][CH:29]=[CH:16][CH:4]=4)[CH2:27][C:2]=3[C:7]=2[C:8]#[N:9])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 11558406HCID 11558406, compound

Product 1

HCID 58409939HCID 58409939, compound

Procedure

A mixture of 2-oxo-4-(piperidin-1-yl)-6-p-tolyl-2H-pyran-3-carbonitrile (294 mg), indanone-2, (132 mg) and NaH (29 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 162-164° C.; ESMS 365 (M++1); IR (KBr) 2213 cm−1 (CN); HRMS calcd. for C26H24N2 364.1940 found 364.1936.

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-d11555e15135400986166b0991ae6865
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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