Triethylamine → HCID 68600119, compound

HRID 1952271Notes

Reaction equation

HRID 1952271 reaction equation
[CH2:1]([O:4][C:5]1[C:6](=[O:12])[CH:7]=[CH:8][C:9](=[O:11])[CH:10]=1)[CH:2]=[CH2:3].[CH:13]([C:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=1)=[CH2:14].C(N(CC)CC)C>CO>[CH2:1]([O:4][C:5]1[C:6](=[O:12])[C:7]2[C:8](=[CH:14][CH:13]=[C:15]3[C:16]=2[CH2:17][CH2:18][CH2:19][CH2:20]3)[C:9](=[O:11])[CH:10]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17497VinylcyclohexeneHCID 469118002-[(Prop-2-en-1-yl)oxy]cyclohexa-2,5-diene-1,4-dione

Product 1

HCID 68600119HCID 68600119, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Allyloxy-1,4-benzoquinone (10.0 g, 60.9 mM) and 1-Vinylcyclohexene (19.8 g, 183 mM) were dissolved in 100 ml of MeOH, and refluxed for 3 hours. The reaction solution was cooled to room temperature, and then Triethylamine (5 ml) and NaIO4 (13.0 g, 61.0 mM) were added thereto, and stirred vigorously for another 1 hours. Reaction solution therein was filtered and the filtrate was concentrated by distillation under reduced pressure and was then purified by chromatography on silica gel to give 7.6 g (28.4 mM) of 3-Allyloxy-5,6,7,8-tetrahydro-1,4-phenanthrenequinone.

Workup

  1. temperaturerefluxed for 3 hours
  2. customReaction solution
  3. filtrationtherein was filtered
  4. concentrationthe filtrate was concentrated by distillation under reduced pressure
  5. customwas then purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8f6dac3f163d431da81869cfc16fbbc8
Source dataset
uspto-grants-2013_03
Patent number
US08404869B2

Reaction notes

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