Tetrahydrofuran → 2-Methoxy-1-(2-methoxyvinyl)naphthalene

HRID 494960Notes

Reaction equation

HRID 494960 reaction equation
CC(C)([O-])C.[K+].[O:7]1[CH2:11]CC[CH2:8]1.[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:35][O:36][C:37]1[CH:46]=[CH:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]=1[CH:47]=O>C(OCC)(=O)C>[CH3:35][O:36][C:37]1[CH:46]=[CH:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]=1[CH:47]=[CH:8][O:7][CH3:11]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 793522-Methoxy-1-naphthaldehydeHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 688531842-Methoxy-1-(2-methoxyvinyl)naphthalene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

While cooling on ice, 0.61 g of potassium t-butoxide was added to 20 ml of a tetrahydrofuran suspension containing 2.28 g of (methoxymethyl)triphenylphosphonium chloride under nitrogen atmosphere. The obtained mixture was stirred for 5 minutes. Thereafter, 600 mg of 2-methoxy-1-naphthaldehyde was added to the reaction solution while cooling on ice. The obtained mixture was stirred at the same temperature for 20 minutes. The reaction solution was diluted with ethyl acetate, and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 667 mg of 2-methoxy-1-(2-methoxyvinyl)naphthalene containing a small amount of triphenylphosphine. This compound was used in the next reaction without further purification.

Workup

  1. temperaturewhile cooling on ice
  2. stirringThe obtained mixture was stirred at the same temperature for 20 minutes
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1f83a66da3b14459bc189c444752ea11
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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