Phenol → HCID 59180450, compound

HRID 1925733Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([O:22][CH3:23])=[O:21])(=[O:13])=[O:12])=[C:7](I)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:25]1([OH:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=NO)C1C(=CC=CC=1)O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C.[Cu-]=O.C(#N)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([O:22][CH3:23])=[O:21])(=[O:13])=[O:12])=[C:7]([O:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 102 (800 mg; 1.66 mmol), phenol (103 mg; 1.09 mmol), salicylaldoxime (45.5 mg; 0.33 mmol), copper(I) oxide (11.8 mg; 0.083 mmol), cesium carbonate (811.3 mg; 2.49 mmol), powdered molecular sieves (300 mg; 3A°) and anhydrous acetonitrile (15 mL) was heated at 85° C. for 16 hours. The reaction mixture was allowed to cool to room temperature and then was diluted with ethyl acetate (20 mL), filtered through a pad of celite and concentrated under reduced pressure. The resulting green residue was purified by automated silica gel chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 15% v/v over 600 mL gradient elution) to yield the title compound as a white solid (201 mg).

Workup

temperatureto cool to room temperature
filtrationfiltered through a pad of celite
concentrationconcentrated under reduced pressure
customThe resulting green residue was purified by automated silica gel chromatography (Biotage®)
washeluting with ethyl acetate/hexanes (0 to 15% v/v over 600 mL gradient elution)

Sources & evidence

ORD record: ord-99a40fd0ae0d4f418f67848dd0909fcb
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178699B2

Reaction notes

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