Water → HCID 86586346, compound

HRID 1359048Notes

Reaction equation

HRID 1359048 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([CH:26]=[CH:27][CH3:28])=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Se](=O)=[O:30].O>O1CCOCC1.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:18][C:17]3[C:19]([CH:26]=[CH:27][CH:28]=[O:30])=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 86586347HCID 86586347, compound

Product 1

HCID 86586346HCID 86586346, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

{(2R)-7-nitro-8-[1-propenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl 4-methylbenzenesulfonate (6.15 g, 15.2 mmole) was dissolved in 180 mL of dioxane. Selenium dioxide (4.20 g, 37.9 mmole) was then added, followed by 0.70 mL of water. The heterogeneous mixture was heated at reflux under nitrogen for 5 hours. Upon cooling, the reaction was filtered and concentrated in vacuum to yield a dark yellow solid. This was dissolved in minimal ethyl acetate and column chromatographed on silica gel using 30% ethyl acetate in hexane as eluant to give 5.75 g of the (R)-enantiomer of the title compound as a light yellow solid (m.p. 138-140° C.).

Workup

  1. temperatureThe heterogeneous mixture was heated
  2. temperatureat reflux under nitrogen for 5 hours
  3. temperatureUpon cooling
  4. filtrationthe reaction was filtered
  5. concentrationconcentrated in vacuum
  6. customto yield a dark yellow solid
  7. customcolumn chromatographed on silica gel using 30% ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-cb3f0fe8e3f24d6f84c8c57b4fb0e852
Source dataset
uspto-grants-2003_07
Patent number
US06599915B2

Reaction notes

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