Diethyl Ether → N-[2-chloro-5-(1-hydroxy-ethyl)-phenyl]-3,4-dimethoxy-benzenesulfonamide

HRID 1674629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1674629
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)(=[O:13])=[O:12].C[Li].[CH3:26]COCC>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:9])[CH3:26])=[CH:4][C:3]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)(=[O:13])=[O:12]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 57511304N-(2-chloro-5-formyl-phenyl)-3,4-dimethoxy-benzenesulfonamideHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 57511305N-[2-chloro-5-(1-hydroxy-ethyl)-phenyl]-3,4-dimethoxy-benzenesulfonamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of N-(2-chloro-5-formyl-phenyl)-3,4-dimethoxy-benzenesulfonamide (1.77 g, 5 mmol) in THF (20 mL) at −78° C. was added dropwise a solution of methyl lithium in ether (1.6 M, 8.6 mL, 2.75 eq). The mixture was stirred at −78° C. for 30 min and then allowed to warm to RT. The mixture was partitioned between EA and NH4Cl solution, the aqueous phase was once more extracted with EA and the combined organic layers were dried over MgSO4 and concentrated. The residue was dried under hv to give the desired product (1.8 g, 100%) as a yellowish oil.

Aufarbeitung

  1. temperatureto warm to RT
  2. customThe mixture was partitioned between EA and NH4Cl solution
  3. extractionthe aqueous phase was once more extracted with EA
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was dried under hv

Quellen und Nachweise

ORD-Eintrag
ord-e0194d3c5ab441e29dd0851840870840
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003654B2

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