Nitromethane → HCID 66777743, compound

HRID 2091020Notes

Reaction equation

HRID 2091020 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.[C:11](Cl)(=[O:16])[CH2:12][CH:13]([CH3:15])[CH3:14].[N+](C)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-]>O>[CH3:14][CH:13]([CH3:15])[CH2:12][C:11]([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:16]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 66054Isovaleryl chlorideHCID 738173-Methylbenzo[b]thiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 66777743HCID 66777743, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 3-methyl-1-benzothiophene (5.00 g), isovaleryl chloride (4.52 mL) and nitromethane (50 mL) was added aluminum (III) chloride (8.98 g) at 0° C., and the mixture was stirred at 0° C. for 30 min then at room temperature for 4 hr. The reaction mixture was poured into ice-cooled water, and the mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19, volume ratio) to give the title object compound (7.72 g, 99%) as a yellow oil.

Workup

  1. waitat room temperature for 4 hr
  2. additionThe reaction mixture was poured into ice-
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with 1N hydrochloric acid and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19, volume ratio)

Sources & evidence

ORD record
ord-dbf0a1b6d781423bbeccf57b9040dcca
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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