Dimethyl Sulfoxide → HCID 59326508, compound

HRID 238638Notes

Reaction equation

HRID 238638 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10](Br)[CH:11]=2)[CH:6]=1.[CH3:29][S:30]([O-:32])=[O:31].[Na+].N1CCC[C@H]1C(O)=O.CS(C)=O>O.[Cu]I>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:30]([CH3:29])(=[O:32])=[O:31])[CH:11]=2)[CH:6]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 67304293HCID 67304293, compound

Product 1

HCID 59326508HCID 59326508, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of [6-bromo-4-(4-ethanesulfonyl-phenoxy)-naphthalen-2-yl]-acetic acid methyl ester (32 mg, 0.07 mmol, methyl ester of example 15-1), sodium methanesulfinate (10 mg, 0.09 mmol), L-proline (4 mg, 0.028 mmol), copper(I) iodide (3 mg, 0.014 mmol) and dimethyl sulfoxide (0.3 mL) was stirred at 115° C. overnight under an argon atmosphere. The resulting mixture was diluted with water (5 mL), and extracted with ethyl acetate (20 mL×2). The combined organic layers were washed with brine (20 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (30% ethyl acetate in petroleum ether) to give [4-(4-ethanesulfonyl-phenoxy)-6-methanesulfonyl-naphthalen-2-yl]-acetic acid methyl ester (11 mg) as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate (20 mL×2)
  2. washThe combined organic layers were washed with brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative TLC (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-cfc49c92642c452883395b759e325991
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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