Sodium hydride → HCID 18385719, compound

HRID 2298329Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:10](=[O:18])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].[H-].[Na+].Br[C:22]([CH3:28])([CH3:27])[C:23](C#N)=[O:24]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[O:18][C:22]([CH3:28])([CH3:27])[C:23](=[O:24])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[S:8][CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 1-{3-bromo4(methylthio)phenyl}-2-phenyl-ethan-1-one (1.54 g) in 50 ml THF, was added 232 mg of 60% oil dispersion of sodium hydride. The mixture was stirred for 1 hour at 0° C., which was followed by dropwise addition of 1.1 ml α-bromoisobutyryl cyanide diluted in 20 ml THF. The reaction mixture was then slowly warmed to room temperature and was stirred overnight. The solvent was removed in vacuo and the resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3). The organic layer was concentrated under reduced pressure and was purified by column chromatography (hexane/ethylacetate=6:1) to yield 1.1 g of 5-{3-bromo-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone. NMR: δ1.55 (s, 6H), 2.47 (s, 3H), 6.99 (d, J=8.7 Hz, 1H), 7.32 (m, 5H), 7.48 (dd, J=8.7, 2.1 Hz, 1H), 7.88 (d, J=1.8 Hz, 1H).

Workup

temperatureThe reaction mixture was then slowly warmed to room temperature
stirringwas stirred overnight
customThe solvent was removed in vacuo
extractionthe resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3)
concentrationThe organic layer was concentrated under reduced pressure
customwas purified by column chromatography (hexane/ethylacetate=6:1)

Sources & evidence

ORD record: ord-7abc435349964012942cba48a5e40879
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492416B1

Reaction notes

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