Tetrahydrofuran → HCID 58409936, compound

HRID 1844882Notes

Reaction equation

HRID 1844882 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[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)O1.[H-].[Na+].[CH2:24]1[CH2:28]O[CH2:26][CH2:25]1>>[C:16]1([C:4]2[C:6]3[C:5]4[C:25](=[CH:24][CH:28]=[CH:16][CH:4]=4)[CH2:26][C:2]=3[C:7]([C:8]#[N:9])=[C:6]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[CH:5]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 11196748HCID 11196748, compound

Product 1

HCID 58409936HCID 58409936, compound

Procedure

A mixture of 2-oxo-6-phenyl-4-(piperidin-1-yl)-2H-pyran-3-carbonitrile (280 mg), indanone-2 (132 mg) and NaH (44 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 140-141° C.; ESIMS 351 (M++1); IR (KBr) 2219 cm−1 (CN); 13C NMR (75.53 MHz, CDCl3): δ 22.89, 24.96, 36.00, 52.15, 100.45, 116.08, 117.93, 120.78, 123.54, 125.06, 125.34, 126.97, 127.35, 127.42, 131.32, 138.85, 139.20, 140.94, 141.01, 149.06, 153.62.

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-233dbb41dc5348a0af640824431c6214
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

Loading…