Methyl morpholine oxide → HCID 85979398, compound

HRID 2221112Notes

Reaction equation

HRID 2221112 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:12]([CH3:18])=[C:13]([CH2:16][OH:17])[S:14][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[C:12]([CH3:18])=[C:13]([CH:16]=[O:17])[S:14][CH:15]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 69270444HCID 69270444, compound

Product 1

HCID 85979398HCID 85979398, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of [4-(4-chloro-benzenesulfonyl)-3-methyl-thiophen-2-yl]-methanol (786 mg, 2.60 mmol), 4-methylmorpholine N-oxide (0.46 g, 3.9 mmol), and powdered 4 Å molecular sieves (1.3 g, activated by brief heating in vacuo) in CH2Cl2 (7 mL) was added tetrapropylammonium perruthenate (46 mg, 0.13 mmol). The resulting mixture was stirred for 1 hour, after which it was filtered through a plug of silica (ca. 25 g) eluting with EtOAc. The eluate was evaporated in vacuo and the product was purified by chromatography on silica gel on a FlashMaster system using as eluent heptane/ethyl acetate (linear gradient elution from 1:0 to 1:1). Fractions containing the product were pooled and evaporated in vacuo to yield the title compound (644 mg, 82%). 1H NMR (CDCl3): 2.60 (s, 3 H), 7.53 (d, J=9.0 Hz, 2 H), 7.87 (d, J=8.5 Hz, 2 H), 8.53 (s, 1 H), 10.01 (s, 1 H).

Workup

  1. filtrationafter which it was filtered through a plug of silica (ca. 25 g)
  2. washeluting with EtOAc
  3. customThe eluate was evaporated in vacuo
  4. customthe product was purified by chromatography on silica gel on a FlashMaster system
  5. additionFractions containing the product
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-32ae01b16d5542328b284a31964818eb
Source dataset
uspto-grants-2008_05
Patent number
US07368472B2

Reaction notes

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