Methoxymethyl-triphenylphosphonium chloride → 2-Isopropyl-6-(4-isopropyl-2-(2-methoxyvinyl)phenyl)naphthalene

HRID 31560Notes

Reaction equation

HRID 31560 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH:22]([CH3:24])[CH3:23])[CH:18]=3)[CH:13]=2)=[C:8]([CH:11]=1)C=O)([CH3:3])[CH3:2].[Cl-].[CH3:26][O:27][CH2:28][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:48](O[K])(C)(C)C>O1CCCC1>[CH:22]([C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:11][C:8]=3[CH:48]=[CH:28][O:27][CH3:26])[CH:13]=2)[CH:18]=1)([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 862261845-Isopropyl-2-(6-isopropyl-2-naphthyl)benzaldehydeHCID 178418922HCID 178418922, compound

Product 1

HCID 688366052-Isopropyl-6-(4-isopropyl-2-(2-methoxyvinyl)phenyl)naphthaleneYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmospheric argon gas flow, 5-isopropyl-2-(6-isopropyl-2-naphthyl)benzaldehyde in an amount of 4.4 g (14 mmol), (methoxymethyl)triphenylphosphoniumchloride in an amount of 5.1 g (15 mmol), t-butoxypotassium in an amount of 1.7 g (15 mmol) and desiccated tetrahydrofuran in an amount of 100 milliliter were placed into a three-necked flask equipped with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was stirred under heating at the room temperature for one night. After the reaction terminated, adding water in an amount of 100 milliliter into the reacted solution, an organic layer was separated, followed by drying with the use of magnesium sulfate. After removing the solvent by distillation by means of a rotary evaporator, the resultant crude product was refined by means of column chromatography (silicagel, hexane/dichloromethane=10/90), and as a result, 4.3 g of an aimed compound (white crystal) was obtained (yield: 90%).

Workup

  1. customwere placed into a three-necked flask
  2. customequipped with a cooling pipe
  3. customAfter the reaction terminated
  4. additionadding water in an amount of 100 milliliter into the reacted solution
  5. customan organic layer was separated
  6. dry with materialby drying with the use of magnesium sulfate
  7. customAfter removing the solvent
  8. distillationby distillation
  9. customby means of a rotary evaporator

Sources & evidence

ORD record
ord-5acbbd5a610e460b8b702bf89d8d63c3
Source dataset
uspto-grants-2008_09
Patent number
US07425653B2

Reaction notes

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