Ammonium Chloride → 1-(2'-Methoxy-5'-fluorophenyl)pent-4-en-1-ol

HRID 1919508Notes

Reaction equation

HRID 1919508 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:4]=1[CH:5]=[O:6].[CH:12]([Mg]Br)=[CH:13][CH2:14][CH3:15].[Cl-].[NH4+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:4]=1[CH:5]([OH:6])[CH2:15][CH2:14][CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27349435-Fluoro-2-methoxybenzaldehydeHCID 178448305HCID 178448305, compound

Product 1

HCID 674998421-(2'-Methoxy-5'-fluorophenyl)pent-4-en-1-olYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methoxy-5-fluorobenzaldehyde (3.0 g, 19.5 mmol) in THF (20 mL) at 0° C. was added a solution 1-butenylmagnesium bromide (0.5 M in THF, 45 mL, 22.5 mmol) dropwise for 15 min. Then the reaction mixture was poured to a solution of saturated ammonium chloride (80 mL) in a separatory funnel. The organic fraction was extracted with ethyl acetate (3×60 mL) and the combined organic layers were washed with brine (50 mL) and dried over sodium sulfate. The solvent then was removed in vacuo and crude product thus obtained was purified by flash column chromatography (10% EtOAc in hexane, Rf=0.11) to give the product as an oil (3.27 g, 93%).

Workup

  1. extractionThe organic fraction was extracted with ethyl acetate (3×60 mL)
  2. washthe combined organic layers were washed with brine (50 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 flash column chromatography (10% EtOAc in hexane, Rf=0.11)

Sources & evidence

ORD record
ord-e0e94cea007a4d7d81192e362ff56e3c
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

Loading…