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

HRID 325191Notes

Reaction equation

HRID 325191 reaction equation
[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

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 5090RofecoxibHCID 8028TetrahydrofuranHCID 11430Potassium Carbonate

Product 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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c5a18eb3f1f343afb394a3a348a0ce3f
Source dataset
uspto-grants-2001_04
Patent number
US06222048B1

Reaction notes

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