Potassium Carbonate → Methyl 4-((3-hydroxy-2,5-dimethylphenyl)sulfanyl)-3-oxobutanoate

HRID 591420Notes

Reaction equation

[CH3:1][C:2]1[C:7]([SH:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].C([O-])([O-])=O.[K+].[K+].Cl[CH2:18][C:19](=[O:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22]>CN(C=O)C>[OH:10][C:3]1[C:2]([CH3:1])=[C:7]([S:8][CH2:18][C:19](=[O:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:6]=[C:5]([CH3:9])[CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 2,5-dimethyl-3-sulfanylphenol (126 mg) and DMF (dry) (8.0 mL) were added K2CO3 (124 mg) and methyl 4-chloro-3-oxobutanoate (0.096 mL) at 0° C. The mixture was stirred at 0° C. for 3 h. The mixture was quenched with water at 0° C. and extracted with EtOAc. The organic layer was washed successively with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (179 mg).

Workup

customThe mixture was quenched with water at 0° C.
extractionextracted with EtOAc
washThe organic layer was washed successively with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record: ord-cebc3bc3d58c4b2384b8f440320ee7d5
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238639B2

Reaction notes

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