Methyl morpholine oxide → HCID 178492628, compound

HRID 1490142Notes

Reaction equation

HRID 1490142 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][C@H:8]2[CH2:11][C@H:10]([CH2:12][OH:13])[CH2:9]2)=[CH:5][CH:4]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][C@H:8]2[CH2:11][C@H:10]([CH:12]=[O:13])[CH2:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 178492629HCID 178492629, compound

Product 1

HCID 178492628HCID 178492628, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of {trans-3-(4-methoxyphenoxy)cyclobutyl}methanol (19.8 g, 95.3 mmol), N-methylmorpholine N-oxide (16.7 g, 143 mmol) and powdered 4A molecular sieves (48 g) in methylene chloride (190 ml) was added solid tetrapropylammonium perruthenate (1.67 g, 4.80 mmol) at room temperature under argon atmosphere. On completion, the mixture was filtered through a pad of silica, eluting with methylene chloride (500 ml). The filtrate was evaporated and the residue purified by silica-gel column chromatography {SiO2, 500 g; hexane/ethyl acetate (3/1)} to afford 12.2 g (62%) of trans-3-(4-methoxyphenoxy)cyclobutanecarbaldehyde as white solids: 1H NMR δ9.88 (s, 1H), 6.88-6.65 (m, 4H), 4.75-4.58 (m, 1H), 3.76 (s, 3H), 3.31-3.15 (m, 1H), 2.82-2.61 (m, 2H), 2.54-2.25 (m, 3H).

Workup

  1. filtrationOn completion, the mixture was filtered through a pad of silica
  2. washeluting with methylene chloride (500 ml)
  3. customThe filtrate was evaporated
  4. customthe residue purified by silica-gel column chromatography {SiO2, 500 g

Sources & evidence

ORD record
ord-e669a649336f41cdb4dc978824df1cfe
Source dataset
uspto-grants-1997_10
Patent number
US05681858

Reaction notes

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