Water → HCID 49764778, compound

HRID 384994Notes

Reaction equation

HRID 384994 reaction equation
C(O[CH:5]1[CH:9]([N+:10]([O-:12])=[O:11])[CH:8]([CH:13]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH3:14])[S:7][CH2:6]1)(=O)C.S(Cl)(Cl)(=O)=O.O>C1(C)C=CC=CC=1>[CH3:17][CH:16]([CH3:18])[CH2:15][CH:13]([C:8]1[S:7][CH:6]=[CH:5][C:9]=1[N+:10]([O-:12])=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 49764905HCID 49764905, compound

Product 1

HCID 49764778HCID 49764778, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
4 °C

Procedure

After dissolving 1.1 g of 5-(4-methylpentan-2-yl)-4-nitrotetrahydrothiophen-3-yl acetate in 7 ml of toluene, the solution was cooled to 4° C. A solution prepared by dissolving 0.8 g of sulfuryl chloride in 2 ml of toluene was added thereto. The temperature of the solution was allowed to rise room temperature, and the solution was stirred for 2 hours. Water was added to stop reaction, and the organic layer was washed with 1 mol/l aqueous sodium hydroxide and saturated saline. The organic layer was dried with magnesium sulfate and concentrated, and then purified by silica gel chromatography (hexane/ethyl acetate=10/1), thereby obtaining 0.8 g of 2-(4-methylpentan-2-yl)-3-nitrothiophene (yield: 85.0%).

Workup

  1. customA solution prepared
  2. additionwas added
  3. customto rise room temperature
  4. customreaction
  5. washthe organic layer was washed with 1 mol/l aqueous sodium hydroxide and saturated saline
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-c07f38563aa84a7c8d254f34f2ce0ef2
Source dataset
uspto-grants-2013_02
Patent number
US08367846B2

Reaction notes

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