Ammonium Chloride → HCID 66778361, compound

HRID 2091044Notes

Reaction equation

HRID 2091044 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]=[O:11])=[C:7]([CH2:12][O:13][CH3:14])[C:6]=2[CH:15]=1.[CH:16]1([Mg]Br)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[Cl-].[NH4+].C[N+]1([O-])CCOCC1>O1CCCC1.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.C(#N)C>[CH:16]1([C:10]([C:8]2[O:9][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:15][C:6]=3[C:7]=2[CH2:12][O:13][CH3:14])=[O:11])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 82029Methyl morpholine oxideHCID 86662730HCID 86662730, compoundHCID 178419651HCID 178419651, compound

Product 1

HCID 66778361HCID 66778361, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (20 mL) of 5-fluoro-3-(methoxymethyl)-1-benzofuran-2-carbaldehyde (1.07 g) synthesized above in tetrahydrofuran was added a 1.0M solution (7.71 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, tetrahydrofuran was evaporated in an evaporator, and the residue 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 (10-50% ethyl acetate/hexane) to give a pale-yellow oil. To a mixture of the obtained oil, 4-methylmorpholine N-oxide (841 mg) and acetonitrile (20 mL) was added tetrapropylammonium perruthenate (126 mg), and the mixture was stirred at room temperature for 1.5 hr and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-20% ethyl acetate/hexane) to give the title object compound (857 mg, 57%) as a colorless oil.

Workup

  1. customto quench
  2. customthe reaction, tetrahydrofuran
  3. customwas evaporated in an evaporator
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (10-50% ethyl acetate/hexane)
  9. customto give a pale-yellow oil
  10. stirringthe mixture was stirred at room temperature for 1.5 hr
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (0-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c311683a6a51455787f9e56fdb3308a7
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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