Ammonium Chloride → HCID 66778911, compound

HRID 2091121Notes

Reaction equation

HRID 2091121 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.[CH:14]1([Mg]Br)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[OH:11])=[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 178419651HCID 178419651, compound

Product 1

HCID 66778911HCID 66778911, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (10 mL) of 5-chloro-3-methyl-1-benzofuran-2-carbaldehyde (600 mg) synthesized above in tetrahydrofuran was added a 1.0M solution (4.62 mL) of cyclohexylmagnesium 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 (15% ethyl acetate/hexane) to give the title object compound (518 mg, 60%) as a pale-yellow 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 (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-697f5aa0ca3b455b9a98e36de6324088
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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