Ammonium Chloride → 8-(5'-Fluoro-2'-methoxyphenyl)oct-1-en-5-ol

HRID 1919520Notes

Reaction equation

HRID 1919520 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH3:14])=[C:6]([CH2:8][CH2:9][CH2:10][CH:11]=[O:12])[CH:7]=1.[CH:15]([Mg]Br)=[CH:16][CH2:17][CH3:18].[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH3:14])=[C:6]([CH2:8][CH2:9][CH2:10][CH:11]([OH:12])[CH2:18][CH2:17][CH:16]=[CH2:15])[CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 252585754-(5-Fluoro-2-methoxyphenyl)butanalHCID 178448305HCID 178448305, compound

Product 1

HCID 252585778-(5'-Fluoro-2'-methoxyphenyl)oct-1-en-5-olYield 63.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(5′-fluoro-2′-methoxyphenyl)butyraldehyde (1.30 g, 6.6 mmol) in THF (15 mL) at 0° C. was added a solution 1-butenylmagnesium bromide (0.5 M in THF, 15 mL, 7.5 mmol) dropwise for 5 min. Then the reaction mixture was poured to a solution of saturated ammonium chloride (60 mL) in a separatory funnel. The organics were extracted with ethyl acetate (3×50 mL) and the combined organic layers were washed with brine (40 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 (12.5% EtOAc in hexane, Rf=0.15) to give the product as a colorless oil (1.06 g, 61%).

Workup

  1. extractionThe organics were extracted with ethyl acetate (3×50 mL)
  2. washthe combined organic layers were washed with brine (40 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 (12.5% EtOAc in hexane, Rf=0.15)

Sources & evidence

ORD record
ord-c1b81c85030e44a9a0d651b82cdf3113
Source dataset
uspto-grants-2012_05
Patent number
US08168635B2

Reaction notes

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