Perchloric Acid → HCID 70818559, compound

HRID 591072Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH:9]([OH:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:8])[S:5][C:6]=1[Cl:7].Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[Na+]>C(OC(=O)C)(C)(C)C>[Br:1][C:2]1[C:3]([CH:9]([O:15][C:3]([CH3:9])([CH3:4])[CH3:2])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:8])[S:5][C:6]=1[Cl:7]

Participants

Conditions

Temperature: -5 °C

Procedure

To a suspension of ethyl 2-(4-bromo-5-chloro-2-methylthiophen-3-yl)-2-hydroxyacetate (44c) (334 mg, 1.065 mmol) in tert-butylacetate (10.9 mL) at −5° C. was added perchloric acid (70%, 0.4 mL). The mixture was stirred at −5° C. for 1 hour then at 0° C. for 30 minutes more. The mixture was stirred at room temperature for 1 hour more and was basified with a saturated aqueous solution of sodium bicarbonate until pH 8. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5) to afford the desired product (44d) as a colorless oil (324 mg, 0.88 mmol, 82%).

Workup

waitat 0° C. for 30 minutes more
stirringThe mixture was stirred at room temperature for 1 hour more
extractionThe aqueous layer was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5)

Sources & evidence

ORD record: ord-ff45c6879a2c430c8d4da3bd6b93b04d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238026B2

Reaction notes

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