4-Iodophenol → HCID 67281982, compound

HRID 1693078Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[I:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25](OS(C)(=O)=O)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[OH-].[Na+]>CN(C)C=O>[I:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:25]2[CH2:26][CH2:27][N:22]([C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])[CH2:23][CH2:24]2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium carbonate (15 g, 109 mmol) was added to a dimethylformamide (200 mL) solution of 4-iodophenol (8.0 g, 36.4 mmol) and 1-t-butoxycarbonyl-4-methanesulfonyloxypiperidine (13.2 g, 47.3 mmol), and stirred at 80° C. for 24 hours. The reaction mixture was cooled to room temperature, then aqueous 2 N sodium hydroxide solution was added to the reaction mixture, and extracted with diethyl ether. The organic layer was washed with saturated brine, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-300, hexane/ethyl acetate=4/1) to obtain the entitled compound (12 g, 82

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with diethyl ether
washThe organic layer was washed with saturated brine
dry with materialdried with anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified through silica gel column chromatography (C-300, hexane/ethyl acetate=4/1)
customto obtain the entitled compound (12 g, 82

Sources & evidence

ORD record: ord-08b7ca92fbc34dd49fc2cca063eb3fb0
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158652B2

Reaction notes

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