Sodium Hydroxide → 6-Carboxy-4,4-ethylenedioxy-5-methylthiochroman-1,1-dioxide

HRID 1275445Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([C:19]([O:21]CC)=[O:20])[C:5]([CH3:18])=[C:6]2[C:11]=1[S:10](=[O:13])(=[O:12])[CH2:9][CH2:8][C:7]12[O:17][CH2:16][CH2:15][O:14]1.[OH-].[Na+]>C(O)C.O.[Zn]>[C:19]([C:4]1[C:5]([CH3:18])=[C:6]2[C:11](=[CH:2][CH:3]=1)[S:10](=[O:13])(=[O:12])[CH2:9][CH2:8][C:7]12[O:17][CH2:16][CH2:15][O:14]1)([OH:21])=[O:20]

Participants

Conditions

Temperature: 60 °C

Procedure

28 Grams (77 mmol) of 8-chloro-6-ethoxycarbonyl-4,4-ethylenedioxy-5-methylthiochroman-1,1-dioxide was dissolved in 100 ml of ethanol, and 13.6 g (208 mmol) of a zinc powder was added. Further, a solution of 27 g (400 mmol) of sodium hydroxide in 50 ml of water and 50 ml of ethanol was added, and then the mixture was stirred under heat at 60° C. for 6 hours. After the completion of the reaction, an insoluble solid was removed by filtration, and an aqueous layer was washed with methylene chloride. The aqueous layer was acidified with a 5 wt % hydrochloric acid aqueous solution and extracted with ethyl acetate, and an organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 16.2 g (yield 69%) of the titled compound.

Workup

customAfter the completion of the reaction
customan insoluble solid was removed by filtration
washan aqueous layer was washed with methylene chloride
extractionextracted with ethyl acetate
washan organic layer was washed with a saturated sodium chloride aqueous solution
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-413f037bc4e64ac4b441f87ed2b62d84
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06159904

Reaction notes

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