Nitromethane → HCID 66777378, compound

HRID 2091280Notes

Reaction equation

HRID 2091280 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[CH2:11]([CH:13]([CH2:17][CH3:18])[C:14](Cl)=[O:15])[CH3:12].[N+](C)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-]>O>[CH2:11]([CH:13]([CH2:17][CH3:18])[C:14]([C:3]1[S:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]=1[CH3:1])=[O:15])[CH3:12]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 738173-Methylbenzo[b]thiopheneHCID 759542-Ethylbutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 66777378HCID 66777378, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-methyl-1-benzothiophene (1.00 g), 2-ethylbutyryl chloride (1.02 mL) and nitromethane (10 mL) was added aluminum chloride (1.35 g) at 0° C., and the mixture was stirred for 3 hr. Water was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-10% ethyl acetate/hexane) to give the title object compound (1.65 g, 99%) as a pale-yellow oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (0-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f20d967a0ff8420d984c4cdc706570b7
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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