Tetrahydrofuran → HCID 58409928, compound

HRID 1844879Notes

Reaction equation

HRID 1844879 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[S:17][CH:18]=[CH:19][CH:20]=2)O1.[H-].[Na+].[CH2:23]1[CH2:27]O[CH2:25][CH2:24]1>>[N:10]1([C:6]2[CH:5]=[C:4]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:25]3[CH2:24][C:23]4[C:27]([C:2]=3[C:7]=2[C:8]#[N:9])=[CH:6][CH:5]=[CH:4][CH:16]=4)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 11449042HCID 11449042, compound

Product 1

HCID 58409928HCID 58409928, compound

Procedure

A mixture of 2-oxo-4-(piperidin-1-yl)-6-(thiophen-2-yl)-2H-pyran-3-carbonitrile (286 mg), indanone-1 (132 mg) and NaH (37 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 Yellowish solid; mp 152-154° C.; ESMS 357 (M++1); IR (KBr). 2217 cm−1 (CN); HRMS calcd. for C23H20N2S 356.1347 found 356.1139.

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-0802f68313434c00864fcf489fc10f21
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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