Water → 3-Cyclopentylmethoxy-2-nitro-5-phenoxy-pyridine

HRID 1966242Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([O:11][CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH:13]1([CH2:12][O:11][C:4]2[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=[C:2]([O:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:3]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

Conditions

Temperature: 100 °C

Procedure

5-Chloro-3-cyclopentylmethoxy-2-nitro-pyridine (1.3 mmol) is dissolved in DMF (10 ml), phenol (3 eq.) and K2CO3 (4 eq.) is added. The reaction is heated to 100° C. in the microwave for 45 min. The reaction solution is pored into water and extracted with methyl-tert.-butyl ether. The combined organic layers are washed with brine, dried over MgSO4 and the solvent is removed in vacuo. 3-Cyclopentylmethoxy-2-nitro-5-phenoxy-pyridine is obtained after column chromatography (heptane/ethyl acetate) as yellow oil in a yield of 94%. HPLC (method C): 2.31 min; LC-MS (method A): 2.48 min, 315.15 (MH+).

Workup

extractionextracted with methyl-tert.-butyl ether
washThe combined organic layers are washed with brine
dry with materialdried over MgSO4
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-6903d7a8dbd943038f7d3b8759cc1896
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420642B2

Reaction notes

Loading…