Water → ({[2,2-Dimethoxy-1-(nitromethyl)ethyl]thio}methyl)benzene

HRID 453579Notes

Reaction equation

HRID 453579 reaction equation
[CH3:1][O:2][CH:3]([O:9][CH3:10])/[CH:4]=[CH:5]/[N+:6]([O-:8])=[O:7].[CH2:11]([SH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1CCCCC1.O>C1(C)C=CC=CC=1>[CH3:1][O:2][CH:3]([O:9][CH3:10])[CH:4]([S:18][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:5][N+:6]([O-:8])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 8082PiperidineHCID 108772663,3-Dimethoxy-1-nitroprop-1-ene

Product 1

HCID 59135946({[2,2-Dimethoxy-1-(nitromethyl)ethyl]thio}methyl)benzeneYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (1E)-3,3-dimethoxy-1-nitroprop-1-ene (3.03 g, prepared according to Tetrahedron 2002, 58, 5773-5778), benzyl mercaptan (2.54 mL) and piperidine (0.25 mL) in toluene (20 mL) was stirred at room temperature for 48 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80) to give the title compound (4.78 g, yield 86%) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80)

Sources & evidence

ORD record
ord-9d8ff99cd94e408f86c7e27db7939946
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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