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

HRID 1421076Notes

Reaction equation

HRID 1421076 reaction equation
[OH:1][C:2]([CH3:16])([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.C([O:20][CH2:21][C:22](Cl)=[O:23])(=O)C.C1CCN2C(=NCCC2)CC1.Cl>CC#N.N1C=CC=CC=1>[CH3:15][C:2]1([CH3:16])[O:1][C:21](=[O:20])[C:22]([OH:23])=[C:3]1[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 26297Acetoxyacetyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 154285142-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-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-27809ef581f64dc6a1db8811621e182c
Source dataset
uspto-grants-2000_06
Patent number
US06071954

Reaction notes

Loading…