ethyl (Z)-3-(4-chlorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)-2-propenoate → 2(3H)-Furanone, 3-((4-chlorophenyl)(4-(methylsulfonyl)phenyl)methylene)dihydro-, (3Z)-

HRID 2393636Notes

Reaction equation

HRID 2393636 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[C:9](/[CH2:15]CO)\[C:10]([O:12][CH2:13]C)=[O:11])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](=[C:9]2\[C:10](=[O:11])[O:12][CH2:13][CH2:15]\2)/[C:18]2[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 11112334ethyl (Z)-3-(4-chlorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)-2-propenoate

Product 1

HCID 98098732(3H)-Furanone, 3-((4-chlorophenyl)(4-(methylsulfonyl)phenyl)methylene)dihydro-, (3Z)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The moist product from Example 64 is heated under reflux in 1.5 1 of toluene in the presence of 1 g of paratoluenesulfonic acid. The water and ethanol are removed with the aid of a Dean Stark apparatus and then about 11 of toluene is evaporated off. After returning to room temperature, the crystals formed are filtered off and washed with a minimal amount of butan-2-one, then dried to give 261.5 g of (Z)-3-[1-(4-chlorophenyl)-1-(4-methanesulfonylphenyl) methylidene)dihydro-furan-2-one in the form of crystals melting at 188°-190° C.

Workup

  1. customThe water and ethanol are removed with the aid of a Dean Stark apparatus
  2. customabout 11 of toluene is evaporated off
  3. customAfter returning to room temperature
  4. customthe crystals formed
  5. filtrationare filtered off
  6. washwashed with a minimal amount of butan-2-one
  7. customdried

Sources & evidence

ORD record
ord-78276bc826de4886976afcaf32222210
Source dataset
uspto-grants-1998_09
Patent number
US05807873

Reaction notes

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