Ammonium Chloride → HCID 66777827, compound

HRID 2091296Notes

Reaction equation

HRID 2091296 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[CH:11]=[O:12].[CH:13]1([Mg]Br)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[Cl-].[NH4+].C[N+]1([O-])CCOCC1>O1CCCC1.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.C(#N)C>[CH:13]1([C:11]([C:3]2[S:4][C:5]3[CH:10]=[CH:9][N:8]=[CH:7][C:6]=3[C:2]=2[CH3:1])=[O:12])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 82029Methyl morpholine oxideHCID 82374292HCID 82374292, compoundHCID 178419651HCID 178419651, compound2×

Product 1

HCID 66777827HCID 66777827, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution (40 mL) of 3-methylthieno[3,2-c]pyridine-2-carbaldehyde (1.87 g) synthesized above in tetrahydrofuran was added a 1.0M solution (21.2 mL) of cyclohexylmagnesium bromide in tetrahydrofuran at 0° C., and the mixture was stirred for 1 hr. A 1.0M solution (10.0 mL) of cyclohexylmagnesium bromide in tetrahydrofuran was additionally added, and the mixture was further stirred at 0° C. 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 (30-90% ethyl acetate/hexane) to give a pale-yellow solid. To a mixture of the obtained solid, 4-methylmorpholine N-oxide (1.24 mg) and acetonitrile (30 mL) was added tetrapropylammonium perruthenate (164 mg), and the mixture was stirred at room temperature for 4 hr, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10-50% ethyl acetate/hexane) to give the title object compound (864 mg, 31%) as a white solid.

Workup

  1. stirringthe mixture was further stirred at 0° C. for 1 hr
  2. customto quench
  3. customthe reaction
  4. extractionthe reaction mixture 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 (30-90% ethyl acetate/hexane)
  9. customto give a pale-yellow solid
  10. stirringthe mixture was stirred at room temperature for 4 hr
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (10-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-51e67b22c9094d8fb00722913f119375
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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