Furan → 1,4-Dihydro-1,4-epoxytriphenylene

HRID 871812Notes

Reaction equation

HRID 871812 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2.[NH2-].[Na+].[O:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1>C1COCC1>[O:18]1[CH:22]2[C:2]3[C:3]4[C:8]([C:9]5[C:14]([C:15]=3[CH:19]1[CH:20]=[CH:21]2)=[CH:13][CH:12]=[CH:11][CH:10]=5)=[CH:7][CH:6]=[CH:5][CH:4]=4

Participants

5

Reactant 3

HCID 8029FuranHCID 113099-BromophenanthreneHCID 24533Sodium amide

Product 1

HCID 126679791,4-Dihydro-1,4-epoxytriphenylene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

9-Bromophenanthrene (18.6 g, 72.3 mmol), sodium amide (8.47 g, 217.0 mmol) were charged in a two-necked bottle. The bottle was then vacuumed and purged with nitrogen, and dried THF (120 mL) and furan (78.1 mL, 1.07 mmol) were added to the bottle. The mixture in the bottle was heated to 70° C. for reaction for 24 hours, and the resulting was filtered to remove metal. The filtrate was condensed to remove the solvent, and then purified by chromatography with hexanes to yield A (14.7 g, 83%) as white solid powder.

Workup

  1. additionwere added to the bottle
  2. filtrationthe resulting was filtered
  3. customto remove metal
  4. customcondensed
  5. customto remove the solvent
  6. custompurified by chromatography with hexanes
  7. customto yield A (14.7 g, 83%) as white solid powder

Sources & evidence

ORD record
ord-6b4fc6286bbf412f8523bb97a8254e73
Source dataset
uspto-grants-2015_03
Patent number
US08974920B2

Reaction notes

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