Diethyl Ether → 1-[3-(3-Thienyl)phenoxy]-5-bromo-2-pentanone

HRID 1464773Notes

Reaction equation

HRID 1464773 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=2)=[CH:2]1.[H-].[Na+].Br[CH2:16][C:17](=[O:22])[CH2:18][CH2:19][CH2:20][Br:21].C(OCC)C>CN(C)C=O.O>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=2)[O:12][CH2:16][C:17](=[O:22])[CH2:18][CH2:19][CH2:20][Br:21])=[CH:2]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 41303433-(Thiophen-3-YL)phenolHCID 229149631,5-Dibromopentan-2-one

Product 1

HCID 199169541-[3-(3-Thienyl)phenoxy]-5-bromo-2-pentanoneYield 10.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

0.25 g of 3-(3-thienyl)phenol was dissolved in 2.5 ml of dimethylformamide, and 28 mg of 60% oily sodium hydride was added. The mixture was stirred at room temperature for 15 minutes, and then a dimethylformamide solution (1 ml) of 0.45 g of 1,5-dibromo-2-pentanone [see J. Chem. Soc., 1948, 278] was added dropwise at -40° C. The mixture was stirred at this temperature for 2 hours, and ethyl ether and water were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane / ethyl acetate=30/1] to give 50 mg of the captioned compound as a colorless oil.

Workup

  1. stirringThe mixture was stirred at this temperature for 2 hours
  2. customThe organic layer separated
  3. customthe product was purified by silica gel column chromatography [hexane / ethyl acetate=30/1]

Sources & evidence

ORD record
ord-d3a44d95929d40c9a0af22aa491fd5df
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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