Tetrabutylammonium Fluoride → 2-Tert-butyl-5-(3-hydroxy-phenyl)-1,1-dioxo-1,2-dihydro-1lambda6-isothiazol-3-one

HRID 724615Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4.08-A (1.39 g, 3.5 mmol) in tetrahydrofuran (14 mL) at 0° C. was treated with tetra-n-butylammonium fluoride (1.1 g, 4.2 mmol) dropwise. The reaction mixture was stirred at 25° C. for 30 min and diluted with ethyl acetate (150 mL) and washed with 0.1 N HCl (100 mL) and brine (50 mL). The organic layer was dried with Na2SO4, filtered, and concentrated to give a crude residue which was purified using flash column chromatography (100% hexane to 30% ethyl acetate/hexane) to yield 4.08-B as a white solid (0.95 g, 96%). 1H NMR (500 MHz, CDCl3): δ 7.39 (dd, J=7.8, 7.8 Hz, 1H), 7.34–7.32 (m, 1H), 7.26–7.24 (m, 1H), 7.05–7.02 (m, 1H), 6.63 (s, 1H), 5.3 (br s, 1H), 1.73 (s, 9H); LCMS found for C13H16NO4S (M+H)+: m/z=282.

Workup

washwashed with 0.1 N HCl (100 mL) and brine (50 mL)
dry with materialThe organic layer was dried with Na2SO4
filtrationfiltered
concentrationconcentrated
customto give a crude residue which
customwas purified

Sources & evidence

ORD record: ord-083a597bdfc841b392a1cbe60847430d
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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