10-Bromo-1-decene → Octadeca-1,17-dien-8-one

HRID 1247711

Reaction equation

HRID 1247711 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[Mg].C[O:14]C[NH-].[C:17](O)(=O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24]>C(OCC)C>[CH2:11]=[CH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4](=[O:14])[CH2:3][CH2:2][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=[CH2:17]

Participants

6

Reactant 4

HCID 54338410-Bromo-1-deceneHCID 5439777-Octenoic acidHCID 5462224MagnesiumHCID 86598838Methoxymethyl amide

Product 1

HCID 21909233Octadeca-1,17-dien-8-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A Grignard solution was prepared under nitrogen from 2.15 g (8.53 mmol) of 10-bromodec-1-ene and 249 mg (10.22 mmol) of magnesium powder in 20 mL of diethyl ether. The fresh Grignard solution was slowly added dropwise under a N2 atmosphere at 0° C. to a solution of 790 mg (4.26 mmol) of the methoxymethyl amide of oct-7-enoic acid and 10 mL of diethyl ether. Stirring was then continued at 20° C. for one hour. The charge was carefully quenched with Na4Cl solution and then extracted twice with diethyl ether. The organic phase was again washed with water, dried and concentrated. Column chromatographic fractionation furnished 820 mg (3.11 mmol) of octadeca-1,17-dien-8-one.

Workup

  1. customThe charge was carefully quenched with Na4Cl solution
  2. extractionextracted twice with diethyl ether
  3. washThe organic phase was again washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3885284bab6645a294d15aba542d01d6
Source dataset
uspto-grants-2006_10
Patent number
US07129380B2

Linked notes

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