Methyl morpholine oxide → HCID 19023661, compound

HRID 1034177Notes

Reaction equation

HRID 1034177 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]([CH2:11][CH2:12][OH:13])[CH2:3][CH2:2]1.C[N+]1([O-])CCOCC1>C(Cl)Cl.C(OCC)(=O)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]([CH2:11][CH:12]=[O:13])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 14330281HCID 14330281, compound

Product 1

HCID 19023661HCID 19023661, compoundYield 65.3%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(3,4-dihydro-2H-1-benzopyran-4-yl)ethanol (1.45g, 8 mmol), N-methylmorpholine-N-oxide (1.41 g, 12 mmol) and 4 A molecular sieves (4.0 g) in methylene chloride (20 ml), tetrapropylammonium perruthenate (0.140 g, 0.4 mmol) was added. The reaction mixture was stirred at room temperature for 15 min., diluted with an equal volume of ethyl acetate (20 ml) and flash filtered through silica gel (eluant: methylene chloride/ethyl acetate 1:1). Concentration of the filtrate in vacuo afforded the title compound as an oily gum (0.92 g, 64%). NMR (300 MHz/CDCl3) 9.87 (1 H, s).

Workup

  1. filtrationfiltered through silica gel (eluant: methylene chloride/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-f765032b66544a018b3dd22bb6617b12
Source dataset
uspto-grants-1994_05
Patent number
US05314895

Reaction notes

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