1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-(5-Chloro-2-pyridyloxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one

HRID 376344Notes

Reaction equation

FC1C=C(F)C=CC=1O[C:5]1[C:6](=[O:22])[O:7][C:8]([CH3:21])([CH3:20])[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([OH:35])=[N:33][CH:34]=1.C1CCN2C(=NCCC2)CC1>CC#N.CCOCC>[Cl:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][C:5]2[C:6](=[O:22])[O:7][C:8]([CH3:20])([CH3:21])[C:9]=2[C:10]2[CH:11]=[CH:12][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:14][CH:15]=2)=[N:33][CH:34]=1

Participants

Conditions

Temperature: 67.5 °C

Procedure

To a mixture of 2-chloroacetic acid 2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one ester (1.0 g, 3.13 mmol, prepared similarly to the compound of example 5, Step 1) and 5-chloro-2-pyridinol (0.41 g, 3.16 mmol) in CH3CN (20 mL) was added DBU (1.5 mL, 10.0 mmol) at r.t.. The mixture was stirred for 1 h, then heated at 65-70° C. for 3 h. The volatile solvents were removed in vacuo. The residue was chromatographed over silica gel and eluted with hexane:EtOAc (1:1) to yield a colorless oily residue which was swished in Et2O to provide the title compound as a white powder (230 mg).

Workup

customThe volatile solvents were removed in vacuo
customThe residue was chromatographed over silica gel
washeluted with hexane:EtOAc (1:1)
customto yield a colorless oily residue which

Sources & evidence

ORD record: ord-01bce1bff4be4804bad32582b7b2179e
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06020343

Reaction notes

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