Water → 4-Tert-butyl-2-(2-oxo-2-phenylethyl)-cyclohexanone

HRID 574136Notes

Reaction equation

HRID 574136 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](N2CCCC2)=[CH:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19].[OH2:26]>CN(C=O)C>[C:1]([CH:5]1[CH2:6][CH2:7][C:8](=[O:26])[CH:9]([CH2:17][C:18](=[O:19])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 1072321-[4-(Tert-butyl)-1-cyclohexen-1-YL]pyrrolidine

Product 1

HCID 122703414-Tert-butyl-2-(2-oxo-2-phenylethyl)-cyclohexanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a 250-mL round-bottomed flask containing 3.3 mL of 1-(4-tert-butylcyclohex-1-enyl)pyrrolidine was added 100 mL anhydrous DMF, under nitrogen. The flask was fitted with an addition funnel containing 2-bromoacetophenone (4.12 gm) in 35 mL anhydrous DMF, which was dripped into the enamine solution over 60 min. This solution was stirred at ambient temperature for 10 hr, then 90 mL water was added to the solution and it was stirred for another 11 hr, 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 sulfate, filtered and rotovapped down to give a yellow oil. The oil was purified by MPLC using 10% ethyl acetate/hexanes.

Workup

  1. customThe flask was fitted with an addition funnel
  2. stirringwas stirred for another 11 hr, 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 sulfate
  6. filtrationfiltered
  7. customto give a yellow oil
  8. customThe oil was purified by MPLC

Sources & evidence

ORD record
ord-66888487893448f38e9deaf36627187f
Source dataset
uspto-grants-2015_05
Patent number
US09034871B2

Reaction notes

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