Methanol → 2-(3,4-Dichlorophenyl)-3-hydroxy-4-methylcarbonyl-2,5-dihyrothiophene

HRID 1949133Notes

Reaction equation

CO.[NH2-].[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:13]([S:18][CH2:19][CH2:20][C:21](=[O:23])[CH3:22])[C:14]([O:16]C)=O)[CH:9]=[CH:10][C:11]=1[Cl:12].[Cl-].[NH4+]>O>[Cl:5][C:6]1[CH:7]=[C:8]([CH:13]2[C:14]([OH:16])=[C:20]([C:21]([CH3:22])=[O:23])[CH2:19][S:18]2)[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

Conditions

Temperature: 40 °C

Procedure

A methanol (500 mL) solution of sodium amide (19.2 g, purity: 90%, 1.5 equivalent amounts based on the starting material) was heated to 40° C., and to this solution, a methanol (200 mL) solution of methyl 2-(3,4-dichlorophenyl)-2-(3-oxobutylthio)acetate (100 g, purity: 95%, 296 mmol) was dropwise added over a period of 12 minutes, followed by stirring at 40° C. for 1 hour. The reaction solution was cooled to 5° C., water (300 mL) was dropwise added over a period of 10 minutes, and then the solvent was distilled off. To the obtained crude product, chloroform and a saturated ammonium chloride aqueous solution were added, followed by liquid separation, and the organic layer was washed with a saturated salt solution and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off to give the desired product as an oil (59.3 g, yield: 65%).

Workup

temperatureThe reaction solution was cooled to 5° C.
distillationthe solvent was distilled off
customTo the obtained crude product, chloroform
customfollowed by liquid separation
washthe organic layer was washed with a saturated salt solution
dry with materialdried over anhydrous magnesium sulfate
customThe drying agent was removed by filtration
distillationthe solvent was distilled off

Sources & evidence

ORD record: ord-ab7b960c34b94f909af9147d38110052
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399685B2

Reaction notes

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