Potassium hydroxy sulfite → HCID 68486052, compound

HRID 1191588Notes

Reaction equation

HRID 1191588 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[C:11]([CH:17]2[C:22](=[O:23])[C:21]([CH3:25])([CH3:24])S[C:19]([CH3:27])([CH3:26])[C:18]2=[O:28])[CH:10]=1.O[O:30][S:31]([O-:33])=O.[K+]>CO.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[C:11]([CH:17]2[C:18](=[O:28])[C:19]([CH3:27])([CH3:26])[S:31](=[O:33])(=[O:30])[C:21]([CH3:25])([CH3:24])[C:22]2=[O:23])[CH:10]=1

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 68486440HCID 68486440, compound

Product 1

HCID 68486052HCID 68486052, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of 4-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethylthiopyran-3,5-dione (79 mg, 0.1816 mmol) and oxone (446 mg, 0.726 mmol) is stirred at ambient temperature for 20 hours as a solution in methanol/water (1 ml, 1:1 ratio). The reaction mixture is then partitioned between water and dichloromethane, the organic phase is separated and concentrated under reduced pressure. The residue is purified by preparative reverse phase HPLC to give 4-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethyl-1,1-dioxo-thiopyran-3,5-dione (24.6 mg) as a clear gum.

Workup

  1. customThe reaction mixture is then partitioned between water and dichloromethane
  2. customthe organic phase is separated
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-7c1252a16a5b4f7e9a8a230b167cd534
Source dataset
uspto-grants-2014_03
Patent number
US08680012B2

Reaction notes

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