Ammonium Chloride → 2-[Cyclohexyl(hydroxy)methyl]-3-methyl-1-benzofuran-5-carbonitrile

HRID 2091155Notes

Reaction equation

HRID 2091155 reaction equation
[CH:1]([C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:6]=2[C:7]=1[CH3:8])=[O:2].[CH:15]1([Mg]Br)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[Cl-].[NH4+]>O1CCCC1>[CH:15]1([CH:1]([OH:2])[C:3]2[O:4][C:5]3[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:6]=3[C:7]=2[CH3:8])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 824063072-Formyl-3-methyl-1-benzofuran-5-carbonitrileHCID 178419651HCID 178419651, compound

Product 1

HCID 667770382-[Cyclohexyl(hydroxy)methyl]-3-methyl-1-benzofuran-5-carbonitrileYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (30 mL) of 2-formyl-3-methyl-1-benzofuran-5-carbonitrile (1.49 g) synthesized above in tetrahydrofuran was added a 1.0M solution (12.1 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 (25% ethyl acetate/hexane), and then purified by NH silica gel column chromatography (ethyl acetate) to give the title object compound (922 mg, 43%) as a pale-yellow solid.

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 (25% ethyl acetate/hexane)
  8. custompurified by NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-ba5c5796d4f24dc5a5f8042e1626eddd
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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