Hydrochloric Acid → 3-(4-Benzyloxy-phenyl)-1,1,1-trifluoro-propan-2-one

HRID 2168617Notes

Reaction equation

HRID 2168617 reaction equation
CO[C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.C[Si](C)(C)[C:22]([F:25])([F:24])[F:23].[F-].[Cs+].Cl>C1COCC1>[CH2:12]([O:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C:3](=[O:19])[C:22]([F:25])([F:24])[F:23])=[CH:10][CH:9]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2756645Methyl 2-(4-benzyloxyphenyl)acetate

Product 1

HCID 673872073-(4-Benzyloxy-phenyl)-1,1,1-trifluoro-propan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (4-benzyloxy-phenyl)-acetic acid methyl ester (11.7 mmol, 3.0 g), trimethyl-trifluoromethyl-silane and cesium fluoride in THF may be stirred at room temperature for 2 h. Hydrochloride may be added upon consumption of ester as indicated by TLC. The mixture may be stirred further at room temperature until the intermediate disappears as indicated by TLC to provide 3-(4-benzyloxy-phenyl)-1,1,1-trifluoro-propan-2-one.

Workup

  1. stirringThe mixture may be stirred further at room temperature until the intermediate

Sources & evidence

ORD record
ord-635bf373a0984232bca548a6e1588bee
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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