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

HRID 1919510Notes

Reaction equation

HRID 1919510 reaction equation
[CH:1]([Mg]Br)=[CH:2][CH2:3][CH3:4].[F:7][C:8]1[CH:9]=[CH:10][C:11]([O:17][CH3:18])=[C:12]([CH2:14][CH:15]=[O:16])[CH:13]=1.[Cl-].[NH4+]>C1COCC1>[CH3:18][O:17][C:11]1[CH:10]=[CH:9][C:8]([F:7])=[CH:13][C:12]=1[CH2:14][CH:15]([OH:16])[CH2:4][CH2:3][CH:2]=[CH2:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 838270332-(5-Fluoro-2-methoxyphenyl)acetaldehydeHCID 178448305HCID 178448305, compound

Product 1

HCID 674994761-(2'-Methoxy-5'-fluorophenyl)hex-5-en-2-olYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-butenylmagnesium bromide (0.5 M in THF, 9 mL, 4.5 mmol) at 0° C. was added a solution of 5-fluoro-2-methoxyphenylacetaldehyde (635 mg, 3.8 mmol) in THF (10 mL) dropwise for 15 min. Then the reaction mixture was poured in to a solution of saturated ammonium chloride (40 mL) in a separatory funnel. The organics were extracted with ethyl acetate (3×50 mL) and the combined organic layers were washed with brine (50 mL) and dried over sodium sulfate. The solvent was removed in vacuo and crude product thus obtained was purified by flash column chromatography (12.5% EtOAc in hexane, Rf=0.18) to give the product as an oil (642 mg, 74%).

Workup

  1. extractionThe organics were extracted with ethyl acetate (3×50 mL)
  2. washthe combined organic layers were washed with brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed in vacuo and crude product
  5. customthus obtained
  6. customwas purified by flash column chromatography (12.5% EtOAc in hexane, Rf=0.18)

Sources & evidence

ORD record
ord-343354cd0aaa497ca8f03be141df5b78
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

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