Phenylsilane → HCID 67237075, compound

HRID 1712111Notes

Reaction equation

HRID 1712111 reaction equation
C1([SiH3])C=CC=CC=1.[C:8]([C:11]1[CH:16]=[CH:15][C:14](/[C:17](/[CH3:22])=[CH:18]/[N+:19]([O-:21])=[O:20])=[CH:13][CH:12]=1)(=[O:10])[CH3:9].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CC(C)([O-])C.[Cu+].C1(C)C=CC=CC=1.C[C@H](P(C1CCCCC1)C1CCCCC1)[C]1[C](P(C2C=CC=CC=2)C2C=CC=CC=2)[CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1.[Fe].O.O1CCCC1>[C:8]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:22])[CH2:18][N+:19]([O-:21])=[O:20])=[CH:13][CH:12]=1)(=[O:10])[CH3:9]

Participants

9

Reactant 3

HCID 12752PhenylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 53472021HCID 53472021, compound

Product 1

HCID 67237075HCID 67237075, compoundYield 86%

Reagents, catalysts & solvents 5

HCID 178461696HCID 178461696, compoundCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolventHCID 11252043AGN-PC-005B6WSolvent

Procedure

In a 10 mL Schlenk-flask, 6.8 mg of copper (I) tert-butoxide and 55 μmol of (S)—(R)-JOSIPHOS were dissolved in 5 ml of toluene. After stirring for 30 minutes at room temperature to give an asymmetric copper complex. This solution to the amount containing 10 μmol of the asymmetric copper complex were mixed with 4.9 ml of toluene. Further, 185 μL of (1.5 mmol) of phenylsilane and 27 μL (1.5 mmol) of water were added thereto. After stirring for 5 minutes, 1 mmol of (E)-2-(4-acetylphenyl)-1-nitro-1-propene was added, and the mixture was further stirred for 24 hours at room temperature. Four milliliters (4 mL) of a tetrahydrofuran solution of tetrabutylammonium fluoride (1 mol/L) were added to the reaction mixture and stirring was continued for 3 hours. Water was added and the mixture was extracted with diethyl ether (30 mL×2). After drying over sodium sulfate, the solvent was evaporated. The residue was purified by flash chromatography (silica gel, hexane/ethyl acetate) to provide optically active 2-(4-acetylphenyl)-1-nitropropane.

Workup

  1. customto give an asymmetric copper complex
  2. additionThis solution to the amount containing 10 μmol of the asymmetric copper complex
  3. stirringAfter stirring for 5 minutes
  4. stirringthe mixture was further stirred for 24 hours at room temperature
  5. stirringstirring
  6. waitwas continued for 3 hours
  7. extractionthe mixture was extracted with diethyl ether (30 mL×2)
  8. dry with materialAfter drying over sodium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by flash chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b5fb32c91a004cf785903a318ad1b4cc
Source dataset
uspto-grants-2010_09
Patent number
US07790900B2

Reaction notes

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