Triethylamine → 2(5H)-Furanone, 3-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-

HRID 1019183Notes

Reaction equation

HRID 1019183 reaction equation
Br[CH2:2][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.CCN(CC)CC.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=[O:31])=[CH:25][CH:24]=1.C1CCN2C(=NCCC2)CC1>C(#N)C.Cl>[F:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[C:30](=[O:32])[O:31][CH2:2][C:3]=2[C:5]2[CH:6]=[CH:7][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:9][CH:10]=2)=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 98372-(4-Fluorophenyl)acetic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 7358232-Bromo-4'-(methylsulfonyl)acetophenone

Product 1

HCID 108303942(5H)-Furanone, 3-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-Yield 68.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

To the product of Step 1 (216 mg) dissolved in acetonitrile (4 mL) was added Et3N (0.26 mL), followed by 4-fluorophenylacetic acid (102 mg). After 1.5 h at room temperature 0.23 nL of DBU was added. The reaction mixture was stirred for another 45 min and then treated with 5 mL of IN HCl. The product was extracted with EtOAc, dried over Na2S04 and concentrated. The residue was purified by flash chromatography (40% EtOAc in hexane) to yield 150 mg of the title compound as a solid. 1H NMR (CD3COCD3) d 3.15 (3H, s), 5.36 (3H, s), 7.18 (2H, J=8.9 Hz, t), 7.46 (2H, m), 7.7 (2H, J=8.65 Hz, d), 7.97 (2H, J=8.68, d).

Workup

  1. extractionThe product was extracted with EtOAc
  2. customdried over Na2S04
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (40% EtOAc in hexane)

Sources & evidence

ORD record
ord-3de4b0d597a240d9854e6f2b3d5ffd18
Source dataset
uspto-grants-2002_11
Patent number
US06486194B2

Reaction notes

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