Tetrahydrofuran → HCID 58409937, compound

HRID 1844885Notes

Reaction equation

HRID 1844885 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2O[C:13](=O)[C:12]([C:16]#[N:17])=[C:11]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:10]=2)=[CH:5][CH:4]=1.[H-].[Na+].[CH2:26]1[CH2:30]O[CH2:28][CH2:27]1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:5]3[C:4]4[C:27](=[CH:26][CH:30]=[CH:8][CH:3]=4)[CH2:28][C:13]=3[C:12]([C:16]#[N:17])=[C:11]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 12169843HCID 12169843, compound

Product 1

HCID 58409937HCID 58409937, compound

Procedure

A mixture of 6-(4-methoxyphenyl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile (310 mg), indanone-2 (132 mg) and NaH (40 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 202-204° C.; MS 380 (M+); IR (KBr) 2210 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-b60af199943a49bf898437ee0c87ebc8
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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