Acetone → HCID 86756584, compound

HRID 322884Notes

Reaction equation

HRID 322884 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[CH:20]=[CH:19][C:18]=1SC)[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[S:32]([O-:37])(O[O-])(=O)=O.[K+].[K+].S(=O)(=O)(O)[O-].[Na+].[CH3:46]C(C)=O>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:16][C:17]1[CH:18]([CH3:19])[C:46](=[S:32]=[O:37])[CH:20]=[C:21]([O:23][CH2:24][C:25]2[CH:29]=[CH:28][S:27][CH:26]=2)[CH:22]=1)[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 4

HCID 180AcetoneHCID 516919Sodium BisulfateHCID 10313463Potassium peroxymonosulphateHCID 54532626HCID 54532626, compound

Product 1

HCID 86756584HCID 86756584, compound

Conditions

Temperature
0 °C

Procedure

A solution of ethyl (RS)-4-(2-methylphenyl)-4-[2-methylthio-5-(3-thienylmethoxy)phenoxy]butanoate in acetone (20 mL), at 0° C. is treated dropwise with a solution of potassium peroxymonosulphate (1.01 g of commercial 2KHSO5:KHSO4:K2SO4). The reaction mixture is stirred at 0° C. for 20 minutes, then treated with saturated aqueous sodium bisulphate solution (20 mL), and extracted with dichloromethane (2×50 mL). The combined organic extracts are dried over magnesium sulphate, filtered and concentrated in vacuo, to give ethyl (RS,RS)-4-(2-methylphenyl)-4-[2-methyl-sulphinyl-5-(3-thienylmethoxy)phenoxy)-butanoate (0.75 g) in the form of a yellow oil.

Workup

  1. extractionextracted with dichloromethane (2×50 mL)
  2. dry with materialThe combined organic extracts are dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5253d454b7844fb7b6906111a53f4200
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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