Sulfuric Acid → HCID 69516013, compound

HRID 1374614Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:18])[C:5](=[O:17])[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)([CH3:9])[CH3:8])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[F:25][C:26]([Si](C)(C)C)([F:28])[F:27].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.S(=O)(=O)(O)O>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:18])[C:5]([OH:17])([C:26]([F:28])([F:27])[F:25])[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)([CH3:9])[CH3:8])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

5.3 g of 4-(3-fluorophenyl)-4-methyl-2-oxovaleric acid-ethyl ester in 60 ml of dimethylformamide is combined at 0° C. with 3.25 g of cesium carbonate and 4.63 ml of trifluoromethyl(trimethyl)-silane. After 1 hour at 0° C. and 16 hours at room temperature, it is cooled again to 0° C. and mixed with 20 ml of a 1 M tetrabutylammonium fluoride solution in tetrahydrofuran. After 30 minutes at 0° C., 2N sulfuric acid and ethyl acetate are added to it, the ethyl acetate phase is washed with water, dried (Na2SO4) and concentrated by evaporation. After chromatography on silica gel hexane-ethyl acetate (20:1) and bulb tube distillation, 4.45 g of 4-(3-fluorophenyl)-2-hydroxy-4-methyl-2-trifluoromethylvaleric acid-ethyl ester is obtained (boiling point 100° C./0.04 hPa).

Workup

waitAfter 30 minutes at 0° C.
washthe ethyl acetate phase is washed with water
dry with materialdried (Na2SO4)
concentrationconcentrated by evaporation
distillationAfter chromatography on silica gel hexane-ethyl acetate (20:1) and bulb tube distillation

Sources & evidence

ORD record: ord-520ad8b7174f422d8d338a2da7f02d0a
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07166592B2

Reaction notes

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