1,4-Dioxane → HCID 10134858, compound

HRID 889844Notes

Reaction equation

HRID 889844 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:16]=[CH:15][C:14](Br)=[C:13]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn].[O:29]1CCO[CH2:31][CH2:30]1>>[CH2:1]([O:8][C:9](=[O:10])[C:11]1[CH:16]=[CH:15][C:14]([C:30](=[O:29])[CH3:31])=[C:13]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 5352426Tin atomHCID 15345889HCID 15345889, compound

Product 1

HCID 10134858HCID 10134858, compound

Conditions

Temperature
100 °C

Procedure

In dioxane was placed 4-bromo-1,3-benzenedicarboxylate dibenzyl ester (1.78 g, 4.2 mmol), tri-n-butyl(1-ethoxyvinyl), tin (1.70 g, 4.7 mmol), and bis-triphenylphosphine palladium (II) dichloride (175 mg, 0.25 mmol). The mixture was warmed to 100° C. and stirred for 24 hours. The dark solution was evaporated at reduced pressure to give an oil. The oil was purified by MPLC (90 g silica gel, 3:1 [hexane:ethyl acetate]). This gave 0.91 g of the ethoxyvinyl intermediate. This was then placed into a solution of acetic acid (25 mL) and water (5%) and stirred for 1 hour. The mixture was evaporated in vacuo to give an oil which was purified by MPLC (90 g silica gel, 8:2 [hexane: ethyl acetate]). This gave 699 mg (43%) of a white solid. MS: M+1=389.2.

Workup

  1. customThe dark solution was evaporated at reduced pressure
  2. customto give an oil
  3. customThe oil was purified by MPLC (90 g silica gel, 3:1 [hexane:ethyl acetate])
  4. stirringstirred for 1 hour
  5. customThe mixture was evaporated in vacuo
  6. customto give an oil which
  7. customwas purified by MPLC (90 g silica gel, 8:2 [hexane: ethyl acetate])

Sources & evidence

ORD record
ord-c417b68c3a6840ba931de19bb720f5db
Source dataset
uspto-grants-2006_02
Patent number
US06995151B2

Reaction notes

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