Ammonium Chloride → HCID 66777169, compound

HRID 2091273Notes

Reaction equation

HRID 2091273 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][CH2:14][CH2:15][O:16][CH3:17])[C:6]=2[CH:18]=1.[CH:19]1([Mg]Br)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[Cl-].[NH4+].C[N+]1([O-])CCOCC1>O1CCCC1.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.C(#N)C>[CH:19]1([C:10]([C:8]2[O:9][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:18][C:6]=3[C:7]=2[CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])=[O:11])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 82029Methyl morpholine oxideHCID 86662751HCID 86662751, compoundHCID 178419651HCID 178419651, compound

Product 1

HCID 66777169HCID 66777169, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (20 mL) of 5-fluoro-3-[(2-methoxyethoxy)methyl]-1-benzofuran-2-carbaldehyde (1.33 g) synthesized above in tetrahydrofuran was added a 1.0M solution (7.91 mL) of cyclohexylmagnesium bromide in tetrahydrofuran at 0° C., and the mixture was stirred for 2 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 (0-40% ethyl acetate/hexane) to give a pale-yellow oil. To a mixture of the obtained oil, 4-methylmorpholine N-oxide (933 mg) and acetonitrile (20 mL) was added tetrapropylammonium perruthenate (140 mg), and the mixture was stirred overnight at room temperature, 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 (881 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 (0-40% ethyl acetate/hexane)
  8. customto give a pale-yellow oil
  9. stirringthe mixture was stirred overnight at room temperature
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (0-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e68374b7307449b182605b183038105e
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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