Ammonium Chloride → 1-(1-phenylcyclopropyl)ethanone

HRID 478142Notes

Reaction equation

HRID 478142 reaction equation
CN(C)[C:3]([C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[CH3:15][Li].[Cl-].[NH4+]>C1COCC1>[C:8]1([C:5]2([C:3](=[O:4])[CH3:15])[CH2:7][CH2:6]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 18000813HCID 18000813, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 122572631-(1-phenylcyclopropyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

4.34 g of 27 is dissolved in 189 ml of THF, cooled to −10° C., and 21.5 ml of methyllithium solution (1.6 M in diethyl ether) is added in drops under nitrogen. It is stirred for 2 hours at this temperature, and the reaction mixture is then poured into saturated ammonium chloride solution. After extraction with ethyl acetate, the organic phase is dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 3.7 g of title compound 28 is obtained as a yellowish oil.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. customthe organic phase is dried on sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customThe residue is chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-172ab3ec24fc4a839c216dfc1c9de412
Source dataset
uspto-grants-2003_11
Patent number
US06642218B2

Reaction notes

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