Formaldehyde → 5-Hydroxymethyl-4-(4-(methylsulfonyl)phenyl)-3-phenyl-2-(5H)-furanone

HRID 325191

Reaktionsgleichung

Reaktionsgleichung von HRID 325191
[C:1]1([C:7]2[C:8](=[O:22])[O:9][CH2:10][C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23]=[O:24].C1C[O:28][CH2:27]C1.[C:30]([O-])([O-])=[O:31].[K+].[K+]>O>[OH:28][CH2:27][CH:10]1[O:9][C:8](=[O:22])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:11]1[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.[OH:24][CH2:23][C:10]1([CH2:30][OH:31])[O:9][C:8](=[O:22])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:11]1[C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 5090RofecoxibHCID 8028TetrahydrofuranHCID 11430Potassium Carbonate

Produkt 2

HCID 220026365-Hydroxymethyl-4-(4-(methylsulfonyl)phenyl)-3-phenyl-2-(5H)-furanoneHCID 220026535,5-bis(hydroxymethyl)-3-phenyl-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-phenyl-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone from Step 1 (0.31 g, 1.0 mmol), 37% aqueous formaldehyde solution (0.1 mL), THF (20 mL) and water (5 mL) was treated with K2CO3 (20 mg, 0.15 mmol). After stirring for 1 h at room temperature, the reaction mixture was quenched with 15 mL of saturated aqueous NH4Cl and extracted with 50 mL of EtOAc. The extract was dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 3:1 EtOAc/hexanes to give 50 mg of the title compound along with 120 mg of 5,5-bis(hydroxymethyl)-3-phenyl-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone.

Aufarbeitung

  1. customthe reaction mixture was quenched with 15 mL of saturated aqueous NH4Cl
  2. extractionextracted with 50 mL of EtOAc
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 3:1 EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c5a18eb3f1f343afb394a3a348a0ce3f
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06222048B1

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