Bromoethene → HCID 14261103, compound

HRID 1085657Notes

Reaction equation

HRID 1085657 reaction equation
[CH:1]1([CH2:7][CH:8]=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:10]([Mg]Br)=[CH2:11].[Mg].C(Br)=C.[Cl-].[NH4+]>O.C1COCC1>[CH:1]1([CH2:7][CH:8]([OH:9])[CH:10]=[CH2:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 11641BromoetheneHCID 25517Ammonium ChlorideHCID 3166272-CyclohexylacetaldehydeHCID 5462224MagnesiumHCID 178418507HCID 178418507, compound

Product 1

HCID 14261103HCID 14261103, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 60 g (0.47 mol) of cyclohexylacetaldehyde in 400 ml of abs. THF is added dropwise at -20° to a solution of vinylmagnesium bromide in abs. THF, prepared from 13.8 g (0.57 mol) of magnesium and 66.3 g (0.62 mol) of vinyl bromide in 500 ml of abs. THF. When the addition is complete, the whole is stirred for 30 minutes at -20° and then hydrolysed with 900 ml of saturated ammonium chloride solution. After diluting with 250 ml of H2O, the reaction mixture is extracted three times with 1 liter of ether each time, washed three times with 500 ml of brine each time, dried with MgSO4 and then concentrated by evaporation in a rotary evaporator. The residue is distilled at 50°/0.1 mbar.

Workup

  1. additionWhen the addition
  2. extractionthe reaction mixture is extracted three times with 1 liter of ether each time
  3. washwashed three times with 500 ml of brine each time
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated by evaporation in a rotary evaporator
  6. distillationThe residue is distilled at 50°/0.1 mbar

Sources & evidence

ORD record
ord-207ae8b811c04f419c97e9c4c0d324c1
Source dataset
uspto-grants-1991_04
Patent number
US05010189

Reaction notes

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