Methoxymethyl-triphenylphosphonium chloride → HCID 68520612, compound

HRID 658243Notes

Reaction equation

HRID 658243 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li]CCCC.[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([CH:44]=[C:45]([CH:47]=O)[CH:46]=1)[C:40]([O:42][CH3:43])=[O:41])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([CH:44]=[C:45]([CH:47]=[CH:2][O:3][CH3:4])[CH:46]=1)[C:40]([O:42][CH3:43])=[O:41])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 24813624HCID 24813624, compoundHCID 178418339Butyllithium

Product 1

HCID 68520612HCID 68520612, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of (methoxymethyl)(triphenyl)phosphonium chloride (1.5 eq.) in THF (0.1 M) at −78° C. was added n-BuLi (1.5 eq.) dropwise. The reaction was stirred at −78° C. for 30 min and then added a solution of methyl 3-(benzyloxy)-5-formylbenzoate (1 eq.) from the previous step in THF. After stirring at rt for 40 min, the reaction was quenched with saturated aqueous NH4Cl solution. The aqueous layer was extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 15% EtOAc in Hex) to afford a mixture of E- and Z-methyl 3-(benzyloxy)-5-[2-methoxyvinyl]benzoate.

Workup

  1. stirringAfter stirring at rt for 40 min
  2. customthe reaction was quenched with saturated aqueous NH4Cl solution
  3. extractionThe aqueous layer was extracted with ether
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash column chromatography (SiO2, 15% EtOAc in Hex)
  8. customto afford

Sources & evidence

ORD record
ord-3b5ae1a568704be3978e18528846e976
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Reaction notes

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