Ammonium Chloride → 1-(3-Ethyl-1-benzofuran-2-yl)-3-methylbutan-1-ol

HRID 2091018Notes

Reaction equation

HRID 2091018 reaction equation
[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH:12]=[O:13])[CH3:2].O1CCCC1.[CH2:19]([Mg]Br)[CH:20]([CH3:22])[CH3:21].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH:12]([OH:13])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 126115243-Ethyl-1-benzofuran-2-carbaldehydeHCID 178420648HCID 178420648, compound

Product 1

HCID 667789351-(3-Ethyl-1-benzofuran-2-yl)-3-methylbutan-1-olYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (50 mL) of 3-ethyl-1-benzofuran-2-carbaldehyde (2.27 g) synthesized above in tetrahydrofuran was added dropwise 1.0M isobutylmagnesium bromide tetrahydrofuran solution (19.5 mL) at 0° C., and the mixture was stirred for 1 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:17, volume ratio) to give the title object compound (1.55 g, 51%) as a yellow oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:17, volume ratio)

Sources & evidence

ORD record
ord-dad972e7dce74bf7b542bc92372952bf
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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