Hydrochloric Acid → 2,2-Dimethyl-5-[1-(4-o-tolylmethanesulfinyl-phenyl)-but-2-ynyl]-[1,3]dioxane-4,6-dione

HRID 1993044Notes

Reaction equation

[OH:1]O.[CH3:3][C:4]1([CH3:31])[O:9][C:8](=[O:10])[CH:7]([CH:11]([C:15]2[CH:20]=[CH:19][C:18]([S:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[CH:17][CH:16]=2)[C:12]#[C:13][CH3:14])[C:6](=[O:30])[O:5]1.O.Cl>CC(O)=O>[CH3:3][C:4]1([CH3:31])[O:9][C:8](=[O:10])[CH:7]([CH:11]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[O:1])=[CH:17][CH:16]=2)[C:12]#[C:13][CH3:14])[C:6](=[O:30])[O:5]1

Participants

Conditions

Temperature: 80 °C

Procedure

Hydrogen peroxide (20 μL, 0.05 mmol) was added to a 0° C. solution of 28.3 (20 mg, 0.05 mmol) in AcOH (2 mL). The reaction was stirred at 80° C. for 1.5 hours, then cooled to room temperature and stirred for 16 hours. The reaction mixture was poured into cold water and the resulting solution was acidified to pH=2 with 6N HCl(aq). The aqueous layer was extracted with ethyl acetate and sec-butanol. The combined organic layers were concentrated to yield 10 mg (50%) of 2,2-Dimethyl-5-[1-(4-o-tolylmethanesulfinyl-phenyl)-but-2-ynyl]-[1,3]dioxane-4,6-dione (29.1). LC/MSD m/e: 383.0 (consistent with di-acid-H).

Workup

temperaturecooled to room temperature
stirringstirred for 16 hours
extractionThe aqueous layer was extracted with ethyl acetate and sec-butanol
concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record: ord-29efc7b33d89499487876e8a05722a07
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649110B2

Reaction notes

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