Ammonium Chloride → 1-(1-phenylcyclopropyl)ethanone

HRID 1349356Notes

Reaction equation

HRID 1349356 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-f3c2d8351f5f48d4a34b006c12ff17d6
Source dataset
uspto-grants-2007_05
Patent number
US07211680B2

Reaction notes

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