Diisopropyl Ether → HCID 15754338, compound

HRID 1084653Notes

Reaction equation

HRID 1084653 reaction equation
CS[C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[C:6]([N:9]1[CH2:13][C:12]([CH3:14])=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]1=[O:21])([CH3:8])[CH3:7].O[O:26][S:27]([O-:29])=O.[K+].[CH:31](OC(C)C)(C)C>CO.O>[CH3:31][S:27]([C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[C:6]([N:9]1[CH2:13][C:12]([CH3:14])=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]1=[O:21])([CH3:7])[CH3:8])(=[O:29])=[O:26]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 19978933HCID 19978933, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 15754338HCID 15754338, compoundYield 62.3%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
5 °C

Procedure

A methanol/water (1/1) solution of 2.2 g (0.0065 mol) of 1-(3-methylthio-α,α-dimethylbenzyl)-4-methyl-3-phenyl-3-pyrrolin-2-one (Compound No. 364) prepared in accordance with the method of Example 2, was cooled to 5° C., and 30 ml of an aqueous solution of 12 g (0.020 mol) of Oxone was dropwise added thereto at a temperature not higher than 5° C. The mixture was stirred at 5° C. for 2 hours and then at room temperature for further 2 hours. 200 ml of ice water and 100 ml of isopropyl ether were added thereto, and the mixture was stirred for 10 minutes. Then, the product was isolated by filtration and washed with diethyl ether to obtain 1.5 g (yield: 62.3%) of the desired compound as white crystals.

Workup

  1. custom364) prepared in accordance with the method of Example 2
  2. customhigher than 5° C
  3. waitat room temperature for further 2 hours
  4. stirringthe mixture was stirred for 10 minutes
  5. customThen, the product was isolated by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-784fed4216b74c918c72d157225bc915
Source dataset
uspto-grants-1991_04
Patent number
US05006157

Reaction notes

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