Ammonium Chloride → Methyl 9-hydroxy-10-undecenate

HRID 395930Notes

Reaction equation

HRID 395930 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 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of methyl 9-oxononanate (260.4 mg) in THF (4 ml) was dropwise added 0.95M vinyl magnesium bromide (1.62 ml) at —70° C. and then stirred for 1 hour at −60° C. The reaction mixture was poured into a saturated ammonium chloride aqueous solution and then extracted with ethyl acetate. 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 (144 mg, 47.4%).

Workup

  1. customat —70° C.
  2. extractionextracted with ethyl acetate
  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-e564a34b95834516b6aeddaadeac987f
Source dataset
uspto-grants-2003_08
Patent number
US06605741B2

Reaction notes

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