Sodium hydride → HCID 18385936, compound

HRID 2298333Notes

Reaction equation

HRID 2298333 reaction equation
[Cl: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>[Cl: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

5

Reactant 3

HCID 24758Sodium hydrideHCID 124878382-Bromo-2-methylpropanoyl cyanideHCID 18385797HCID 18385797, compound

Product 1

HCID 18385936HCID 18385936, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.6 g of 1-{3-chloro-4-(methylthio)phenyl}-2-phenyl-ethanone in 100 ml dry THF was stirred at 0° C. for 20 minutes in the presence of 60% oil dispersion of sodium hydride (1.5 g), which was followed by dropwise addition of α-bromoisobutyryl cyanide (3.0 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 3.2 g of 5-{3-chloro-4-(methylthio)phenyl}-2,2-dimethyl-4-phenyl-3(2H)-furanone. NMR: δ1.52 (s, 6H), 2.45 (s, 3H), 7.17 (d, J=8.4 Hz, 1H), 7.25 (m, 3H), 7.32 (m, 2H), 7.87 (dd, J=8.4, 1.8 Hz, 1H), 7.97 (d, J=1.8 Hz, 1H). IR (cm−1): 1694, 1613, 1592, 1389, 1252, 1145, 1128.

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-bb148c674de04b0fbbf549327cb40e39
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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