Ammonium Chloride → HCID 66777421, compound

HRID 2091162Notes

Reaction equation

HRID 2091162 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]=[O:11])=[C:7]([CH3:12])[C:6]=2[CH:13]=1.[CH2:14]([Mg]Br)[CH:15]([CH3:17])[CH3:16].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([OH:11])[CH2:14][CH:15]([CH3:17])[CH3:16])=[C:7]([CH3:12])[C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 47369825-Chloro-3-methyl-1-benzofuran-2-carbaldehydeHCID 178418816HCID 178418816, compound

Product 1

HCID 66777421HCID 66777421, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (20 mL) of 5-chloro-3-methyl-1-benzofuran-2-carbaldehyde (1.00 g) synthesized in Example A88(2) in tetrahydrofuran was added a 1.0M solution (10.3 mL) of isobutylmagnesium bromide in tetrahydrofuran at 0° C., and the mixture was stirred for 1 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction 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 (20% ethyl acetate/hexane) to give the title object compound (650 mg, 50%) as a colorless oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction 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 (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0593f3c38ebd4f2990b6ea2a2c5d9488
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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