HCID 10953851, compound → (3-Nitroprop-1-en-2-yl)benzene

HRID 1712112Notes

Reaction equation

HRID 1712112 reaction equation
[N+:1](/[CH:4]=[C:5](/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)\[CH3:6])([O-:3])=[O:2].[N+](CC(C1C=CC=CC=1)C)([O-])=O>>[N+:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[CH2:6])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 10953851HCID 10953851, compoundHCID 11400973(1-Methyl-2-nitroethyl)benzene

Product 1

HCID 14321245(3-Nitroprop-1-en-2-yl)benzeneYield 4%

Procedure

In a 10 mL Schlenk-flask, 8 mg of copper (I) chloride and 8 mg of sodium tert-butoxide and 110 mg of (S)-p-tol-BINAP were dissolved in 6 ml of toluene. After stirring for 15 minutes at room temperature to give an asymmetric copper complex. Into this solution, 360 μL (6.0 mmol) of poly(methylhydrosiloxane) (15-40 mPas (20° C.), d=1.004 g/mL, nD20=1.398, produced by Fluka) and 32 mg of water were added. After stirring for 5 minutes, 1.5 mmol of (E)-1-nitro-2-phenyl-1-propene were added, and the mixture was further stirred for 22 hours at room temperature. 1H-NMR analysis showed that the objective optically active 1-nitro-2-phenylpropane was provided in 50% yield. A by-product, 1-nitro-2-phenyl-2-propene was provided in 4% yield.

Workup

  1. additionwere added
  2. stirringthe mixture was further stirred for 22 hours at room temperature
  3. customwas provided in 50% yield

Sources & evidence

ORD record
ord-8e7ffe6c758a46efa377df0eceeb1126
Source dataset
uspto-grants-2010_09
Patent number
US07790900B2

Reaction notes

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