Potassium Carbonate → HCID 118659596, compound

HRID 1477249Notes

Reaction equation

HRID 1477249 reaction equation
[CH3:1][C:2]([S:21]([CH3:24])(=[O:23])=[O:22])([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][Si](C)(C)C)=[CH:11][CH:10]=1)[C:3]([O:5][CH3:6])=[O:4].C([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl>[C:15]([C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][C:2]([CH3:1])([S:21]([CH3:24])(=[O:22])=[O:23])[C:3]([O:5][CH3:6])=[O:4])=[CH:14][CH:13]=1)#[CH:16]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 131736482HCID 131736482, compound

Product 1

HCID 118659596HCID 118659596, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of methyl 2-methyl-2-(methylsulfonyl)-4-(4-((trimethylsilyl)ethynyl)phenyl)butanoate (9.4, 4.4 g, 12.0 mmol) in methanol (80 mL) was added K2CO3 (100 mg, 0.720 mmol) and the reaction was stirred at room temperature for 3 hr. The reaction mixture was filtered through celite, concentrated under reduced pressure to give a residue, which was dissolved in DCM, filtered and concentrated under reduced pressure to yield methyl 4-(4-ethynylphenyl)-2-methyl-2-(methylsulfonyl)butanoate (9.5, 2.49 g, 70.5%). MS: m/z calcd for C15H18O4S 294.09. found [M+H]+ 295.2.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated under reduced pressure
  3. customto give a residue, which
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a70b082863b74290894b4c6c079d3273
Source dataset
uspto-grants-2016_08
Patent number
US09403758B2

Reaction notes

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