Cesium carbonate → Trifluoro-methanesulfonic acid 3-acetyl-5-hydroxy-phenyl ester

HRID 417041Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]([O:18]S(C(F)(F)F)(=O)=O)[CH:7]=[C:8]([O:10][S:11]([C:14]([F:17])([F:16])[F:15])(=[O:13])=[O:12])[CH:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[C:1]([C:4]1[CH:9]=[C:8]([O:10][S:11]([C:14]([F:17])([F:15])[F:16])(=[O:13])=[O:12])[CH:7]=[C:6]([OH:18])[CH:5]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Trifluoro-methanesulfonic acid 3-acetyl-5-trifluoromethanesulfonyloxy-phenyl ester (9.9 g) was dissolved in 1,2-dimethoxyethane (80 mL), followed by addition of cesium carbonate (11.6 g). The resulting suspension was stirred at 80° C. for 3 h and then quenched with saturated solution of ammonium chloride. The solution was then extracted with diethyl ether and combined etherate extracts were washed with brine, dried over anhydrous sodium sulfate, and filtered through a silica pad. The filtrate was concentrated under reduced pressure and purified on a silica gel column using ethyl acetate and hexanes to afford 3.5 g of the title compound (52% yield). HRMS calcd for C19H7O5S1F3 [M+H]+ 285.0039, observed 285.0039.

Workup

customquenched with saturated solution of ammonium chloride
extractionThe solution was then extracted with diethyl ether
washwere washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered through a silica pad
concentrationThe filtrate was concentrated under reduced pressure
custompurified on a silica gel column

Sources & evidence

ORD record: ord-2d33793ae83049e9a01678e22d748a9d
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088936B2

Reaction notes

Loading…