4-Methylbenzenethiol → HCID 57655908, compound

HRID 911752Notes

Reaction equation

HRID 911752 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C>[CH3:12][C:13]([CH3:16])([CH3:15])[CH2:14][S:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 78114-MethylbenzenethiolHCID 24758Sodium hydrideHCID 84953Propane, 1-iodo-2,2-dimethyl-

Product 1

HCID 57655908HCID 57655908, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-methyl-benzenethiol (1.5 g, 12.08 mmol) in anhydrous DMF (6 mL). Cool the solution to 0° C., add sodium hydride (435 mg, 17.21 mmol, 95%) and stir the mixture under nitrogen atmosphere for 15 mm. Add 1-iodo-2,2-dimethylpropane (1.93 mL, 14.5 mmol), stir the mixture for 1 h at 0° C., warm to room temperature and stir overnight. Add water and extract the aqueous phase twice with EtOAc. Wash the combined organic extracts twice with iced-water, dry over Na2SO4, filter and concentrate in vacuo to give the desired intermediate (1.476 g, 63% yield).

Workup

  1. temperaturewarm to room temperature
  2. stirringstir overnight
  3. extractionAdd water and extract the aqueous phase twice with EtOAc
  4. washWash the combined organic extracts twice with iced-water
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f2e61e41305e451dbaf2e6869b09ada0
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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