Benzenesulfinic acid → 2-Benzenesulphonyl-5-(3,4-dimethoxyphenyl)tetrahydrofuran

HRID 22483

Reaktionsgleichung

Reaktionsgleichung von HRID 22483
[C:1]1([S:7]([OH:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Ca+2].[Cl-].[CH3:13][O:14][C:15]1[CH:16]=[C:17](C=[CH:27][C:28]=1[O:29][CH3:30])[CH2:18][CH:19]1[CH2:23][CH2:22][CH:21](OC)[O:20]1>C(Cl)Cl>[C:1]1([S:7]([CH:21]2[CH2:22][CH2:23][CH:19]([C:18]3[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[C:28]([O:29][CH3:30])[CH:27]=3)[O:20]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 12057Benzenesulfinic acidHCID 5284359Calcium ChlorideHCID 199304672-(3,4,Dimethoxybenzyl)-5-methoxytetrahydrofuran

Produkt 1

HCID 199304722-Benzenesulphonyl-5-(3,4-dimethoxyphenyl)tetrahydrofuranAusbeute 36,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of benzenesulphinic acid (8.68 g, 0.061M) in DCM (120 ml) containing a suspension of powdered calcium chloride (1.0 g) at room temperature was added a solution of 2-(3,4,dimethoxybenzyl)-5-methoxytetrahydrofuran (7.0 g, 0.029M) in DCM (80 ml). The mixture was stirred at room temperature for 4 h, quenched by washing with water (2×50 ml), dried over anhydrous sodium sulphate, filtered and evaporated. Column chromatography (flash silica gel; 3:2 hexane/ethyl acetate) provided the product (Rf 0.3) as a clear oil which was crystalized from ethyl acetate/hexane to give 2-benzenesulphonyl-5-(3,4-dimethoxyphenyl)tetrahydrofuran (3.5 g, 35%).

Aufarbeitung

  1. customquenched
  2. washby washing with water (2×50 ml)
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customColumn chromatography (flash silica gel; 3:2 hexane/ethyl acetate) provided the product (Rf 0.3) as a clear oil which
  7. customwas crystalized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c38f96003c364f5190b59bc55a281cd6
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428168

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