Tetrahydrofuran → HCID 58409923, compound

HRID 1844880Notes

Reaction equation

HRID 1844880 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1O[C:10](=O)[C:9]([C:13]#[N:14])=[C:8]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:7]=1.[H-].[Na+].[CH2:23]1[CH2:27]O[CH2:25][CH2:24]1>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:4]2[C:3]3[C:24](=[CH:23][CH:27]=[CH:6][CH:2]=3)[CH2:25][C:10]=2[C:9]([C:13]#[N:14])=[C:8]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 44425423HCID 44425423, compound

Product 1

HCID 58409923HCID 58409923, compound

Procedure

A mixture of 6-(furan-2-yl)-2-oxo-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile (270 mg), indanone-2 (132 mg) and NaH (28 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 160-162° C.; ESIMS 341 (M++1); IR (KBr) 2218 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-4c0b97db0e1d42eaae71bee933bfd86a
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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