Sodium hydride → HCID 58409927, compound

HRID 1844875Notes

Reaction equation

HRID 1844875 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][CH:19]=[CH:18][CH:17]=2)O1.[H-].[Na+]>C1COCC1>[C:16]1([C:4]2[C:5]3[CH2:4][C:16]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:2]=3[C:7]([C:8]#[N:9])=[C:6]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[CH:5]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 11196748HCID 11196748, compound

Product 1

HCID 58409927HCID 58409927, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-oxo-6-phenyl-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile (280 mg), indanone-1 (132 mg) and NaH (36 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 156-156° C.; ESIMS 351 (M++1); IR (KBr) 2214 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-fc117095c70c4030aad6a4fc0fad68d5
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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