Hydrochloric Acid → HCID 23506271, compound

HRID 1841543Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10](Br)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:16][C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].Cl.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10]([O:16][C:17]2[CH:27]=[CH:26][CH:25]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:18]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

3-Benzyloxy-2-bromopyridine (8 g, 30 mmol) and ethyl 3-hydroxybenzoate (13.3 g, 80 mmol) are dissolved in DMF (50 ml), and thereto are added potassium carbonate (28 g, 0.2 mol) and cuprous bromide (11.5 g, 80 mmol). The mixture is heated under reflux at 140° C. for one hour. After being allowed to cool, the reaction solution is acidified with a 15% aqueous hydrochloric acid solution (50 ml), and then neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate (300 ml×2). The organic layer is washed with a saturated brine (200 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to give 3-benzyloxy-2-(3-ethoxycarbonyl-phenoxy)pyridine as a pale yellow oil.

Workup

temperatureThe mixture is heated
temperatureto cool
extractionextracted with ethyl acetate (300 ml×2)
washThe organic layer is washed with a saturated brine (200 ml×2)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record: ord-b0533d0417844252bebfcf68ba78311a
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683186B2

Reaction notes

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