Hydrochloric Acid → 5-Hydroxy-4-(4-methanesulfonyl-phenyl)-5-methyl-3-phenyl-5H-furan-2-one

HRID 2295097Notes

Reaction equation

HRID 2295097 reaction equation
Br[CH:2]([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:16]1([CH2:22][C:23]([OH:25])=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1CCN2C(=NCCC2)CC1.[O:37]=O.Cl>CC#N.[Cl-].[Na+].O.CCN(CC)CC>[OH:37][C:2]1([CH3:15])[O:24][C:23](=[O:25])[C:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[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

9

Reactant 5

HCID 313Hydrochloric AcidHCID 977OxygenHCID 999Phenylacetic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 132078392-Bromo-1-[4-(methanesulfonyl)phenyl]propan-1-one

Product 1

HCID 214727535-Hydroxy-4-(4-methanesulfonyl-phenyl)-5-methyl-3-phenyl-5H-furan-2-one

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2-bromo-1-(4-methylsulfonylphenyl)-propan-1-one (prepared using the methodology of WO 9500501, Ex. 9 Step 1) (8.7 g) and phenyl acetic acid (5 g) in 150 mL of CH3CN was treated with 8.5 mL of Et3N. The reaction mixture was stirred overnight at r.t. and then 12 mL of DBU was added dropwise over 2 min. After stirring for 1 h at r.t. O2 was bulbed into the mixture until it became colorless (in 45 min.). The reaction mixture was then poured into a solution of 80 mL 1N HCl and 100 mL of brine, and extracted with 500 mL of 1:1 EtOAc/hexane. The extract was dried over MgSO4, filtered and concentrated. The crude product was swished from 1:4 EtOAc/hexane (200 mL) to give 7.2 g of the title product as a white solid.

Workup

  1. customprepared
  2. stirringAfter stirring for 1 h at r.t
  3. custom(in 45 min.)
  4. extractionextracted with 500 mL of 1:1 EtOAc/hexane
  5. dry with materialThe extract was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4399f650e5344cf29384a69496af2cb1
Source dataset
uspto-grants-1997_11
Patent number
US05691374

Reaction notes

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