Ammonium Chloride → 1-(5-Fluoro-2-methoxyphenyl)hept-5-en-3-ol

HRID 1919515Notes

Reaction equation

HRID 1919515 reaction equation
[CH:1]([Mg]Br)=[CH:2][CH2:3][CH3:4].[F:7][C:8]1[CH:9]=[CH:10][C:11]([O:18][CH3:19])=[C:12]([CH2:14][CH2:15][CH:16]=[O:17])[CH:13]=1.[Cl-].[NH4+]>C1COCC1>[CH3:19][O:18][C:11]1[CH:10]=[CH:9][C:8]([F:7])=[CH:13][C:12]=1[CH2:14][CH2:15][CH:16]([OH:17])[CH2:1][CH:2]=[CH:3][CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 25258572Benzenepropanal, 5-fluoro-2-methoxy-HCID 178448305HCID 178448305, compound

Product 1

HCID 674997401-(5-Fluoro-2-methoxyphenyl)hept-5-en-3-olYield 172.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-butenylmagnesium bromide (0.5 M in THF, 18 mL, 9.0 mmol) at 0° C. was added a solution of 3-(5′-fluoro-2′-methoxyphenyl)propionaldehyde (3.0 g, 16.5 mmol) in THF (30 mL) dropwise for 15 min. The reaction mixture was poured into a solution of saturated ammonium chloride (80 mL) in a separatory funnel. The organic function was extracted with ethyl acetate (3×80 mL) and the combined organic layers were washed with brine (80 mL) and dried over sodium sulfate. The solvent then was removed in vacuo and crude product thus obtained was purified by a flash column chromatography (15% EtOAc in hexane, Rf=0.20) to give the product as an oil (3.7 g, 94%).

Workup

  1. extractionThe organic function was extracted with ethyl acetate (3×80 mL)
  2. washthe combined organic layers were washed with brine (80 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent then was removed in vacuo and crude product
  5. customthus obtained
  6. customwas purified by a flash column chromatography (15% EtOAc in hexane, Rf=0.20)

Sources & evidence

ORD record
ord-178e504f98df4a11988ee93ea317ba1c
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

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