Sodium hydride → HCID 18385662, compound

HRID 2298323Notes

Reaction equation

HRID 2298323 reaction equation
[F: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>[CH3:27][C:22]1([CH3:28])[C:23](=[O:24])[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:4]2[CH:5]=[CH:6][C:7]([S:8][CH3:9])=[C:2]([F:1])[CH:3]=2)[O:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11817819HCID 11817819, compoundHCID 124878382-Bromo-2-methylpropanoyl cyanide

Product 1

HCID 18385662HCID 18385662, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-{3-fluoro-4-(methylthio)phenyl}-2-phenyl-ethan-1-one (1.68 g) in 100 ml dry THF, was added portion-wise at 0° C. 60% oil dispersion of sodium hydride (270 mg). The reaction solution was stirred at the same temperature for 1 hour. Then 1.2 ml of α-bromo-isobutyryl cyanide diluted in 25 ml dry THF was added dropwise to the stirred solution at 0° C. The reaction mixture was stirred overnight while warming gradually to room temperature. The solution was concentrated in vacuo, to which was added 50 ml water. The aqueous solution was extracted with dichloromethane (50 ml×3). The organic layer was concentrated in vacuo and purified by column chromatography (hexane/ethylacetate=6:1) to give 1.21 g of 2,2-dimethyl-5-{3-fluoro-4-(methylthio)phenyl}-4-phenyl-3(2H)-furanone. NMR: δ1.55 (s, 6H), 2.48 (s, 3H), 7.26-7.39 (m, 7H), 7.67 (m, 1H), 7.81 (m, 1H). IR (cm−1): 1696, 1421, 1388, 1238.

Workup

  1. additionwas added dropwise to the stirred solution at 0° C
  2. stirringThe reaction mixture was stirred overnight
  3. concentrationThe solution was concentrated in vacuo, to which
  4. additionwas added 50 ml water
  5. extractionThe aqueous solution was extracted with dichloromethane (50 ml×3)
  6. concentrationThe organic layer was concentrated in vacuo
  7. custompurified by column chromatography (hexane/ethylacetate=6:1)

Sources & evidence

ORD record
ord-5c14a1a25d1c440d895a040a73ebf614
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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