Tetrahydrofuran → HCID 72332051, compound

HRID 2274127Notes

Reaction equation

HRID 2274127 reaction equation
C([C:3]1[CH:8]=[CH:7][CH:6]=C[C:4]=1[C:9]1[C:10]2[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[CH:22]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=O.[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:46]1[CH2:50][O:49][CH2:48][CH2:47]1.[K]>O>[CH3:48][O:49][CH:50]=[CH:46][C:47]1[CH:6]=[CH:7][CH:8]=[CH:3][C:4]=1[C:9]1[C:10]2[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[CH:22]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 5462222PotassiumHCID 15506413HCID 15506413, compound

Product 1

HCID 72332051HCID 72332051, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under the atmosphere of argon, 25.0 g of 9-(2-formylphenyl)phenanthrene, 33.4 g of methoxymethyltriphenylphosphonium chloride and 300 mL of THF were placed, and 11.9 g of potassium t-buthoxide was added at room temperature during stirring. After stirring at room temperature for 2 hours, 200 mL of water was added. The reaction solution was extracted with diethyl ether, and an aqueous phase was removed. An organic phase was washed with water and saturated saline, and dried with magnesium sulfate. After filtering off magnesium sulfate, the organic phase was concentrated. The residues were purified by silica gel column chromatography, whereby 24.0 g (yield 87%) of 9-[2-(2-methoxyvinyl)phenyl]phenanthrene as an intended product was obtained.

Workup

  1. stirringAfter stirring at room temperature for 2 hours
  2. extractionThe reaction solution was extracted with diethyl ether
  3. customan aqueous phase was removed
  4. washAn organic phase was washed with water and saturated saline
  5. dry with materialdried with magnesium sulfate
  6. filtrationAfter filtering off magnesium sulfate
  7. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-25a2a6809313498fa3bfd0d8f92bef37
Source dataset
uspto-grants-2015_09
Patent number
US09126943B2

Reaction notes

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