Acetone → 2-Hydroxy-2-methyl-1-o-tolylpropane-1-sulfonamide

HRID 339851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339851
COC1C=C(OC)C=CC=1C[NH:6][S:7]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])(=[O:9])=[O:8].C[Li].[CH3:26][C:27]([CH3:29])=[O:28].FC(F)(F)C(O)=O>C1COCC1.C(OCC)C>[OH:28][C:27]([CH3:29])([CH3:26])[CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[S:7]([NH2:6])(=[O:8])=[O:9]

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 68291409N-(2,4-Dimethoxybenzyl)-C-o-tolylmethanesulfonamideHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 682925202-Hydroxy-2-methyl-1-o-tolylpropane-1-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under inert gas, 0.95 g of N-(2,4-dimethoxybenzyl)-C-o-tolylmethanesulfonamide was initially charged in 20 ml of THF, and then, at a temperature of −78° C., 4.06 ml of a 1.6 N methyllithium solution in diethyl ether were added dropwise and the mixture was stirred at constant temperature for 10 minutes. Subsequently, 1.22 ml of acetone were added. After stirring for 10 minutes, the reaction solution was admixed with 2 ml of trifluoroacetic acid and allowed to warm up to room temperature, and the solvent was removed under reduced pressure. The residue was dissolved in 10 ml of dichloromethane, and 1.5 ml of trifluoroacetic acid were added. After stirring at room temperature for 1.5 hours, the reaction solution was concentrated by rotary evaporation and the residue was taken up in a mixture of water and dichloromethane. The solid which precipitates out was filtered off with suction and discarded. The organic phase was dried over MgSO4 and concentrated by rotary evaporation. Since the product was also present in the aqueous phase of the filtrate, this was extracted twice with 50 ml of ethyl acetate, and the combined organic phases were dried over MgSO4 and concentrated by rotary evaporation. Both residues were purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation (516 mg). This gave the product with a molecular weight of 243.3 g/mol (C11H17NO3S).

Aufarbeitung

  1. stirringAfter stirring for 10 minutes
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in 10 ml of dichloromethane
  4. addition1.5 ml of trifluoroacetic acid were added
  5. stirringAfter stirring at room temperature for 1.5 hours
  6. concentrationthe reaction solution was concentrated by rotary evaporation
  7. additionthe residue was taken up in a mixture of water and dichloromethane
  8. customThe solid which precipitates out
  9. filtrationwas filtered off with suction
  10. dry with materialThe organic phase was dried over MgSO4
  11. concentrationconcentrated by rotary evaporation
  12. extractionthis was extracted twice with 50 ml of ethyl acetate
  13. dry with materialthe combined organic phases were dried over MgSO4
  14. concentrationconcentrated by rotary evaporation
  15. customBoth residues were purified by means of normal phase chromatography
  16. concentrationconcentrated by rotary evaporation (516 mg)
  17. customThis gave the product with a molecular weight of 243.3 g/mol (C11H17NO3S)

Quellen und Nachweise

ORD-Eintrag
ord-2e81e9c04775450cad0464780df0b068
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895547B2

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