Bromoethene → 1,3-Decadien-5-one

HRID 372216

Reaction equation

HRID 372216 reaction equation
[CH:1](Br)=[CH2:2].[Mg].CN(C)[CH:7]=[CH:8][C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>O1CCCC1.CCOCC>[CH2:1]=[CH:2][CH:7]=[CH:8][C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 11641BromoetheneHCID 5462224MagnesiumHCID 545630821-(Dimethylamino)-1-octen-3-one

Product 1

HCID 542493721,3-Decadien-5-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Grignard reagent prepared from vinyl bromide (10.7 g), and magnesium (2.43 g) in dry tetrahydrofuran (40 ml) is added gradually a solution of 1-(dimethylamino)-1-octen-3-one (16.9 g), described in Example 37, in dry tetrahydrofuran (20 ml). The mixture is stirred and heated to reflux for 1 hr. The reaction mixture is cooled to room temperature, diluted with ether, washed with hydrochloric acid (10 ml), followed by saturated ammonium chloride solution. The ether extract is dried, and the solvent is removed. The residue is chromatographed to yield the title compound, λmaxEtOH 260nm (ε = 17,050), γmaxfilm 1686, 1668 cm-1.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hr
  3. washwashed with hydrochloric acid (10 ml)
  4. extractionThe ether extract
  5. customis dried
  6. customthe solvent is removed
  7. customThe residue is chromatographed

Sources & evidence

ORD record
ord-ef67b3db29bc48f38a5ab23fa8274b6b
Source dataset
uspto-grants-1978_05
Patent number
US04089898

Linked notes

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