Sodium hydride → HCID 18385789, compound

HRID 2298340Notes

Reaction equation

HRID 2298340 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Br[C:22]([CH3:28])([CH3:27])[C:23](C#N)=[O:24]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[O:18][C:22]([CH3:28])([CH3:27])[C:23](=[O:24])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 124878382-Bromo-2-methylpropanoyl cyanideHCID 18386010HCID 18386010, compound

Product 1

HCID 18385789HCID 18385789, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.05 g of 1-{2-chloro-4-(methylthio)phenyl}-2-phenyl-ethanone in 60 ml dry THF was stirred at 0° C. for 20 minutes in the presence of 95% oil dispersion of sodium hydride (1.0 g), which was followed by dropwise addition of α-bromoisobutyryl cyanide (2.5 ml) diluted in 50 ml THF. The reaction solution was allowed to warm slowly to room temperature and was stirred overnight. Then the solvent was removed in vacuo, which was followed by extraction with 30 ml water and diethylether (50 ml×3). The organic layer was concentrated under reduced pressure and was purified by column chromatography (hexane/ethylacetate=8:1) to yield 2.73 g of 5-{2-chloro-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone. NMR: δ1.56 (s, 6H), 2.48 (s, 3H), 7.10 (dd, J=8.4, 1.5 Hz, 1H), 7.24 (m, 3H), 7.26 (m, 3H), 7.37 (d, J=1.5 Hz, 1H). IR (cm−1): 1698, 1620, 1394, 1235, 1176, 1144.

Workup

  1. customThen the solvent was removed in vacuo, which
  2. extractionwas followed by extraction with 30 ml water and diethylether (50 ml×3)
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customwas purified by column chromatography (hexane/ethylacetate=8:1)

Sources & evidence

ORD record
ord-f89f71e176514fd785f361e6f2bc3c38
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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