Hydrochloric Acid → 3-Hydroxy-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanone

HRID 1940145Notes

Reaction equation

HRID 1940145 reaction equation
FC1C=C(C=CC=1F)[O:5][C:6]1[C:7](=[O:23])[O:8][C:9]([CH3:22])([CH3:21])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(OCC(Cl)=O)(=O)C.C1CCN2C(=NCCC2)CC1.Cl>CC#N.N1C=CC=CC=1>[CH3:21][C:9]1([CH3:22])[O:8][C:7](=[O:23])[C:6]([OH:5])=[C:10]1[C:11]1[CH:12]=[CH:13][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 26297Acetoxyacetyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 99086243-(3,4-Difluorophenoxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one

Product 1

HCID 155422043-Hydroxy-5,5-dimethyl-4-[4-(methylsulfonyl)phenyl]-2(5H)-furanoneYield 62%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

To a 0° C. solution of the alcohol of Example 1, Step 3 (29.5 g, 122 mmol) in CH3CN (350 mL) were added pyridine (25 mL) and acetoxyacetyl chloride (25 g, 183 mmol). After a period of 7 h at r.t., DBU (31 mL) was added to the reaction mixture. After a period of 1 h at 80° C., a second portion of DBU (35 mL) was added. The reaction mixture was kept at 80° C. for 18 h. The reaction mixture was allowed to cool to r.t. The mixture was poured onto ice-water (2.5 L) containing 100 mL of concentrated HCl. The brown solid was collected and dissolved in hot acetonitrile and was filtered through a plug of silica. The solvent was evaporated and the resultant solid was swished in EtOAc to give the title compound (21.2 g, 62%).

Workup

  1. waitAfter a period of 1 h at 80° C.
  2. waitThe reaction mixture was kept at 80° C. for 18 h
  3. additionThe mixture was poured onto ice-water (2.5 L)
  4. customThe brown solid was collected
  5. dissolutiondissolved in hot acetonitrile
  6. filtrationwas filtered through a plug of silica
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7726e172ea2d438ca94fb18cc8a6c3cf
Source dataset
uspto-grants-1997_12
Patent number
US05698584

Reaction notes

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