Methanol → HCID 22118398, compound

HRID 1275441Notes

Reaction equation

HRID 1275441 reaction equation
[Cl:1][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-].[K+].CO>O>[C:19]([C:4]1[C:5]([CH3:18])=[C:6]2[C:11](=[C:2]([Cl:1])[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

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 22118373HCID 22118373, compound

Product 1

HCID 22118398HCID 22118398, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture containing 1.19 g (3.2 mmol) of 8-chloro-6-ethoxycarbonyl-4,4-ethylenedioxy-5-methylthiochroman-1,1-dioxide, 0.33 g (5.0 mmol) of potassium hydroxide, 8 ml of methanol and 2 ml of water was stirred under heat at 80° C. for 2 hours. After the completion of the reaction, 20 ml of water was added, and an aqueous layer was washed with methylene chloride. The aqueous layer was neutralized with 2 wt % hydrochloric acid and extracted with ethyl acetate. An organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off to give 0.92 g (yield 84%) of 6-carboxy-8-chloro-4,4-ethylenedioxy-5-methylthiochroman-1,1-dioxide in the form of a white solid.

Workup

  1. additionwas added
  2. washan aqueous layer was washed with methylene chloride
  3. extractionextracted with ethyl acetate
  4. washAn organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-207722d9311140f08f628ac8f6322b55
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

Loading…