Water → 2-(2-Oxo-2-phenylethyl)cyclohexanone

HRID 2064548Notes

Reaction equation

HRID 2064548 reaction equation
[C:1]1(N2CCCC2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[Na+].[I-].Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17].[OH2:24]>CN1C(=O)CCC1>[O:17]=[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C:1]1=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6259Phenacyl bromideHCID 707681-Pyrrolidino-1-cyclohexene

Product 1

HCID 105128992-(2-Oxo-2-phenylethyl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a 250-mL round-bottomed flask containing 2.4 mL of 1-cyclohex-1-en-1-ylpyrrolidine was added 20 mL anhydrous NMP followed by NaI (0.645 g), under nitrogen. The flask was fitted with an addition funnel containing 2-bromo-1-phenylethanone (4.12 g) dissolved in 35 mL anhydrous NMP, which was dropped into the enamine solution over 60 min. This solution was stirred at ambient temperature for 10 h, then 90 mL of water was added to the solution and it was stirred for another 11 hours, under nitrogen. The solution was then extracted twice with ethyl acetate and water, the organic layers combined and further washed with water (3×), dried over sodium sulphate, filtered and evaporated to give a yellow oil. The oil was purified by Flash chromatography using a gradient cyclohexane:EtOAc (9:1). The product 2-(2-oxo-2-phenylethyl)cyclohexanone was used directly for the next reaction. (4.1 g, 91% yield, 98% purity by HPLC). MS(ESI+): 217.4; MS(ESI−): 215.6.

Workup

  1. customThe flask was fitted with an addition funnel
  2. stirringwas stirred for another 11 hours, under nitrogen
  3. extractionThe solution was then extracted twice with ethyl acetate and water
  4. washfurther washed with water (3×)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a yellow oil
  9. customThe oil was purified by Flash chromatography
  10. customThe product 2-(2-oxo-2-phenylethyl)cyclohexanone was used directly for the next reaction

Sources & evidence

ORD record
ord-00a4906453cb4eb98fa9ed5c7edecf85
Source dataset
uspto-grants-2012_10
Patent number
US08288432B2

Reaction notes

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