HCID 67092093, compound → HCID 86613760, compound

HRID 2264559Notes

Reaction equation

HRID 2264559 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16]3[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[CH:20][C:17]=3[C:18]#[N:19])=[CH:13][C:12]=2[CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16]3[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][C:17]=3[C:18]#[N:19])=[CH:13][C:12]=2[CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67092093HCID 67092093, compound

Product 1

HCID 86613760HCID 86613760, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-(5-Benzylbenzofuran-2-yl)-5-(hydroxymethyl)benzonitrile (0.03 g, 0.09 mmol), Molecular sieves 4A (0.2 g), TPAP (0.0016 mg, 0.004 mmol) and N-morpholino oxide (0.02 g, 0.18 mmol) in acetonitrile was stirred for 1 hour and then filtered through celite to obtain title compound in 93% yield (step 4, Scheme 5): 1H NMR (400 MHz, CDCl3) δ 10.05 (s, 1H), 8.25 (s, 1H), 8.24 (d, 1H), 8.14 (d, 1H), 7.84 (s, 1H), 7.45 (m, 2H), 7.38-7.18 (m, 6H), 4.06 (s, 2H).

Workup

  1. filtrationfiltered through celite

Sources & evidence

ORD record
ord-7a13fba27b454a61b36ed9a3a079e070
Source dataset
uspto-grants-2010_12
Patent number
US07855193B2

Reaction notes

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