Hydrochloric Acid → HCID 70166623, compound

HRID 844017Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=[O:19])[CH:13]=1)[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl.O.C[Si](C)(C)[C:43]([F:46])([F:45])[F:44]>O1CCCC1>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]([OH:19])[C:43]([F:46])([F:45])[F:44])[CH:13]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(3-Formyl-phenoxy)-nicotinic acid ethyl ester (2.0 grams, 7.4 mmole) in 0.5 M trimethyl(trifluoromethyl)silane (18 ml) in tetrahydrofuran (20 ml) at 0° C. was added tetrabutyl ammonium fluoride (0.050 g). The mixture was stirred at 0° C. for 1 hour. To the mixture was added 1.0 N hydrochloric acid (10 ml) and stirred at room temperature for 30 minutes. The mixture was poured into 200 ml water and extracted with diethyl ether. The combined extracts were washed with saturated NaHCO3, and water, dried over magnesium sulfate and concentrated to give an oil which was purified via flash chromatography on silica using 60% ethyl acetate/hexane as eluent to give an oil (1.97 g). MW 341.31; MS (m/e) 341 (M+).

Workup

stirringstirred at room temperature for 30 minutes
extractionextracted with diethyl ether
washThe combined extracts were washed with saturated NaHCO3, and water
dry with materialdried over magnesium sulfate
concentrationconcentrated
customto give an oil which
customwas purified via flash chromatography on silica using 60% ethyl acetate/hexane as eluent

Sources & evidence

ORD record: ord-4ca01e43aa694b548929bb06ca43735f
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380218B1

Reaction notes

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