Water → 1-(2-Oxo-2-phenyl-ethyl)-3,4-dihydro-1H-naphthalen-2-one

HRID 574133Notes

Reaction equation

HRID 574133 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][C:12]=1N1CCCC1.[OH2:26]>C1(C)C=CC=CC=1>[O:3]=[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:1][CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][C:12]1=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 888891-(3,4-Dihydro-2-naphthyl)pyrrolidine

Product 1

HCID 122703441-(2-Oxo-2-phenyl-ethyl)-3,4-dihydro-1H-naphthalen-2-oneYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of phenacylbromide (5.21 g, 26.1 mmol) in toluene (16 mL) was added over 15 minutes to a boiling, stirred solution of 1-(3,4-dihydro-2-naphthyl)pyrrolidine (5.21 g, 26.2 mmol) in toluene (17 mL). The reaction was refluxed 3 hours, diluted with water (15 mL) and refluxed for 4 hours then cooled. The layers were separated and the aqueous phase was extracted with toluene and dried over MgSO4 and concentrated. The material was purified by MPLC using a gradient from 0 to 20% ethyl acetate/hexanes to afford 4.85 g (70% yield) title product as a yellow oil.

Workup

  1. temperatureThe reaction was refluxed 3 hours
  2. temperaturerefluxed for 4 hours
  3. temperaturethen cooled
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with toluene
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe material was purified by MPLC

Sources & evidence

ORD record
ord-8e0c7071463f475db0bd0c6a1b40e761
Source dataset
uspto-grants-2015_05
Patent number
US09034871B2

Reaction notes

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