Potassium Carbonate → HCID 53357168, compound

HRID 714499Notes

Reaction equation

HRID 714499 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:24])[C:8]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)=[C:9]([CH3:13])[S:10]2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:24])[C:8]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[C:9]([CH3:13])[S:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67366890HCID 67366890, compound

Product 1

HCID 53357168HCID 53357168, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Synthesis: Step 1: Synthesis of methyl 4-(7-methoxy-2-methyl-4-oxo-4H-thiochromen-3-yl)benzoate: To a solution of Intermediate F (methyl 4-(2-(2-(acetylthio)-4-methoxyphenyl)-2-oxoethyl)benzoate) (600 mg, 1.674 mmol) in acetone (12 ml) was added K2CO3 (386 mg, 3.348 mmol) at room temperature. The mixture was stirred for 3 hours, filtered and concentrated. The residue was purified by Combi-Flash (40 g silica gel, start PE/EtOAc=10/0 to 3/1 gradient, 40 ml/min, 40 min, 1.6 L total solvent volume) to afford the product as a yellow solid (400 mg, 70%). MS (ESI): m/z 341.0 [M+1]+.

Workup

  1. customSynthesis
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by Combi-Flash (40 g silica gel, start PE/EtOAc=10/0 to 3/1 gradient, 40 ml/min, 40 min, 1.6 L total solvent volume)

Sources & evidence

ORD record
ord-74afaae2ef3b4142a6b369d969058130
Source dataset
uspto-grants-2015_11
Patent number
US09187447B2

Reaction notes

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