1,4-Dioxane → HCID 86654355, compound

HRID 339696Notes

Reaction equation

HRID 339696 reaction equation
[Br:1][C:2]1[C:11]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:20])=[N:9]2)=[CH:4][CH:3]=1.[O:21]1CCOCC1>>[Br:1][C:2]1[C:11]([O:12][Si:13]([C:16]([CH3:17])([CH3:19])[CH3:18])([CH3:14])[CH3:15])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:20]=[O:21])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 312751,4-Dioxane2×HCID 67230584HCID 67230584, compound

Product 1

HCID 86654355HCID 86654355, compoundYield 89%

Conditions

Temperature
80 °C

Procedure

A slurry of SeO2 (0.869 g, 7.83 mmol) and 1,4-dioxane (20 mL) was warmed to 80° C. and then the product from Step B (2.3 g, 6.53 mmol) was added as a 1,4-dioxane solution (20 mL). The mixture was stirred at 80° C. for 32 hours. The mixture was cooled to ambient temperature and filtered through GF/F filter paper and the residual solid was washed with CH2Cl2. The filtrate was concentrated and purified by passing through a silica gel plug, eluting with 50% CH2Cl2/hexane to provide 2.14 g (89%) of the product as a yellow/orange solid.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered through GF/F
  3. filtrationfilter paper
  4. washthe residual solid was washed with CH2Cl2
  5. concentrationThe filtrate was concentrated
  6. custompurified
  7. washeluting with 50% CH2Cl2/hexane

Sources & evidence

ORD record
ord-415751660c814a779649359d84f4405d
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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