Tetrahydrofuran → HCID 58409953, compound

HRID 1844895Notes

Reaction equation

HRID 1844895 reaction equation
O=[C:2]1O[C:6]2[C:8]3[C:13]([CH2:14][C:5]=2[C:4]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:3]1[C:21]#[N:22])=[CH:12][CH:11]=[CH:10][CH:9]=3.[H-].[Na+].[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1>>[CH3:27][O:28][C:29]1[CH:25]=[CH:26][C:4]2[CH2:5][C:6]3[C:2](=[C:3]([C:21]#[N:22])[C:4]([N:15]4[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]4)=[C:5]4[CH2:14][C:13]5[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=5)[C:6]4=3)[C:3]=2[CH:2]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 67393714HCID 67393714, compound

Product 1

HCID 58409953HCID 58409953, compound

Procedure

A mixture of 2-oxo-4-(piperidin-1-yl)-2,5-dihydroindeno[1,2-b]pyran-3-carbonitrile (292 mg), 6-methoxyindanone-1 (162 mg) and NaH (48 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 216-218° C.; IR (KBr) 2213 cm−1 (CN); MS (ESI) 392 (M+); 13C NMR (150 MHz, CDCl3) δ 24.39, 26.94, 35.47, 36.96, 53.14, 55.54, 99.39, 110.62, 113.05, 118.84, 122.72, 123.26, 124.94, 127.11, 127.93, 131.65, 132.25, 134.54, 140.38, 142.59, 144.41, 144.74, 146.32, 152.27, 160.02.

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-296b2dadc9b047ceae6ff10cc35d9b07
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

Loading…