Ammonium Chloride → Methyl 9-hydroxy-10-undecenate

HRID 395931Notes

Reaction equation

HRID 395931 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].[CH:14]([Mg]Br)=[CH2:15].[Cl-].[NH4+]>C1COCC1>[OH:1][CH:2]([CH:14]=[CH2:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 74732Methyl 9-oxononanoateHCID 178418507HCID 178418507, compound

Product 1

HCID 11127632Methyl 9-hydroxy-10-undecenateYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

To a solution of methyl 9-oxononanate (5.26 g) in THF (60 ml) was dropwise added 0.95M vinyl magnesium bromide (31.1 ml) at −30° C. and then stirred for 30 minutes at −25° C. The reaction mixture was poured into saturated ammonium chloride aqueous solution and then extracted with diethyl ether. The organic layer was washed with saturated brine, dried over magnesium sulfate anhydride, and then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to give methyl 9-hydroxy-10-undecenate (3.41 g, 56.3%).

Workup

  1. customat −30° C.
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate anhydride
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a6bddf5a98c5421b95f0c0ac48f3d88c
Source dataset
uspto-grants-2003_08
Patent number
US06605741B2

Reaction notes

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