Diethyl Ether → (e)-7-(5-Bromo-2-thienyl)-3-ethyloct-6-en-3-ol

HRID 49319Notes

Reaction equation

HRID 49319 reaction equation
[Br:1][C:2]1[S:6][C:5](/[C:7](/[CH3:16])=[CH:8]/[CH2:9][CH2:10][C:11]([O:13]CC)=O)=[CH:4][CH:3]=1.[CH2:17]([Mg]Cl)[CH3:18].[CH2:21](OCC)[CH3:22]>>[Br:1][C:2]1[S:6][C:5](/[C:7](/[CH3:16])=[CH:8]/[CH2:9][CH2:10][C:11]([CH2:17][CH3:18])([OH:13])[CH2:21][CH3:22])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 131724374Ethyl (e)-5-(5-bromo-2-thienyl)-4-hexenoateHCID 178461633HCID 178461633, compound

Product 1

HCID 17934786(e)-7-(5-Bromo-2-thienyl)-3-ethyloct-6-en-3-ol

Procedure

3.3 g of ethyl (E)-5-(5-bromo-2-thienyl)-4-hexenoate (10.9 mmol) are dissolved in 50 mL of ethyl ether. 22 mL of 2.0 M ethylmagnesium chloride solution (44 mmol) are then added dropwise and the reaction medium is stirred at room temperature for 30 minutes. After treatment with saturated ammonium chloride solution, extraction with ethyl ether and then drying and evaporation of the solvents from the organic phase, the residue obtained is purified by chromatography on a column of silica. A colourless oil is obtained (m=2.4 g; Y=70%).

Workup

  1. extractionAfter treatment with saturated ammonium chloride solution, extraction with ethyl ether
  2. customdrying
  3. customevaporation of the solvents from the organic phase
  4. customthe residue obtained
  5. customis purified by chromatography on a column of silica
  6. customA colourless oil is obtained (m=2.4 g; Y=70%)

Sources & evidence

ORD record
ord-9cabcb9eaaea42339cb7cae831b09958
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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