Tetrahydrofuran → HCID 58409908, compound

HRID 1844891Notes

Reaction equation

HRID 1844891 reaction equation
[F: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[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:25]1[CH2:29]O[CH2:27][CH2:26]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:4]3[C:3]4[C:26](=[CH:25][CH:29]=[CH:7][CH:2]=4)[CH2:27][C:12]=3[C:11]([C:15]#[N:16])=[C:10]([N:17]3[CH2:22][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 668842646-(4-Fluorophenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile

Product 1

HCID 58409908HCID 58409908, compoundYield 81%

Procedure

A mixture of 6-(4-fluorophenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile (298 mg), indanone-2 (132 mg) and NaH (41 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; yield 81%; mp 130-132° C.; ESMS 369 (M++1); IR (KBr) 2216 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-5bc2da072a834885a40918196606b45b
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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