Tetrahydrofuran → HCID 58409935, compound

HRID 1844881Notes

Reaction equation

HRID 1844881 reaction equation
O=[C:2]1[C:7]([C:8]#[N:9])=[C:6]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)O1.[H-].[Na+].[CH2:23]1[CH2:27]O[CH2:25][CH2:24]1>>[C:15]1([C:4]2[C:6]3[C:5]4[C:24](=[CH:23][CH:27]=[CH:15][CH:4]=4)[CH2:25][C:2]=3[C:7]([C:8]#[N:9])=[C:6]([N:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)[CH:5]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 111292452H-Pyran-3-carbonitrile, 2-oxo-6-phenyl-4-(1-pyrrolidinyl)-

Product 1

HCID 58409935HCID 58409935, compound

Procedure

A mixture of 2-oxo-6-phenyl-4-(pyrrolidin-1-yl)-2H-pyran-3-carbonitrile (266 mg), indanone-2 (132 mg) and NaH (38 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 210-212° C.; MS (FAB) 336 (M+); IR (KBr) 2208 cm−1 (CN); 13C NMR (75.53 MHz, CDCl3): δ 24.50, 36.66, 48.88, 90.0, 113.64, 118.40, 119.85, 123.28, 123.92, 125.16, 126.79, 126.90, 127.27, 127.31, 139.10, 139.87, 140.33, 141.29, 147.16, 150.32; HRMS calcd. for C24H20N2 336.16265 Found 336.16232.

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-14e75b2622fb462b9b65871517742e93
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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