Sodium hydride → HCID 18385687, compound

HRID 2298337Notes

Reaction equation

HRID 2298337 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:10](=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].[H-].[Na+].Br[C:23]([CH3:29])([CH3:28])[C:24](C#N)=[O:25]>C1COCC1>[CH3:28][C:23]1([CH3:29])[C:24](=[O:25])[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:10]([C:4]2[CH:5]=[CH:6][C:7]([S:8][CH3:9])=[C:2]([CH3:1])[CH:3]=2)[O:19]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 124878382-Bromo-2-methylpropanoyl cyanideHCID 18385650HCID 18385650, compound

Product 1

HCID 18385687HCID 18385687, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

437 mg of 1-{3-methyl-4-(methylthio)phenyl}-2-(3-fluorophenyl)-ethanone in 50 ml dry THF was stirred with 67 mg of 60% oil dispersion of sodium hydride for an hour at 0° C., which was followed by dropwise addition of 0.8 ml α-bromoisobutyryl cyanide diluted with 25 ml THF. The reaction solution was slowly warmed to room temperature and was stirred overnight. Then the solvent was removed in vacuo and the resulting residue was extracted with 50 ml water and dichloromethane (50 ml×3). The organic layer was concentrated in vacuo and was purified by column chromatography (hexane/ethylacetate=6:1) to yield 312 mg of 2,2-dimethyl-4-(3-fluorophenyl)-5-{3-methyl-4-(methylthio)phenyl}-3(2H)-furanone. NMR: δ1.55 (s, 6H), 2.27 (s, 3H), 2.48 (s, 3H), 7.36 (m, 4H), 7.32 (m, 1H), 7.45 (m, 2H). IR 1694, 1601, 1385, 1260, 1192.

Workup

  1. customThen the solvent was removed in vacuo
  2. extractionthe resulting residue was extracted with 50 ml water and dichloromethane (50 ml×3)
  3. concentrationThe organic layer was concentrated in vacuo
  4. customwas purified by column chromatography (hexane/ethylacetate=6:1)

Sources & evidence

ORD record
ord-e48ef286511b4ad996bfee0b5a1291ee
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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