Methoxymethyl-triphenylphosphonium chloride → HCID 56638333, compound

HRID 485715Notes

Reaction equation

HRID 485715 reaction equation
[CH3:1][C:2]1([CH3:10])[C@@H:4]([CH:5]=O)[C@H:3]1[C:7]([O-:9])=[O:8].[Na+].[Cl-].[CH3:13][O:14][CH2:15][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.P(O)(O)([O-])=O.[Na+]>CN(C)C=O>[CH3:1][C:2]1([CH3:10])[CH:4]([CH:5]=[CH:13][O:14][CH3:15])[CH:3]1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23672064Monosodium phosphateHCID 86740271HCID 86740271, compound

Product 1

HCID 56638333HCID 56638333, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 9 g of 96.5% potassium tert.-butylate in 90 ml of dimethylformamide was added at -60° C. to a solution of 12.58 g of sodium (1R,cis) 2,2-dimethyl-3-formyl-cyclopropane-carboxylate, 350 ml of dimethylformamide and 26.27 g of methoxymethyl triphenylphosphonium chloride and the temperature was allowed to rise to 20° C. with stirring over 90 minutes. The mixture was poured into aqueous monosodium phosphate solution and was extracted with diisopropyl oxide. The combined organic phases were extracted with 100 ml of aqueous N sodium hydroxide and the aqueous extract was stirred at 5° C. with a mixture of diisopropyl oxide and monosodium phosphate. The mixture was diluted with water and the decanted aqueous phase was extracted with diisopropyl oxide. The organic phase was evaporated to dryness under reduced pressure to obtain 5.22 g of (1R,cis)(E+Z) 2,2-dimethyl-3-(2-methoxy-1-ethenyl)-cyclopropane-carboxylic acid.

Workup

  1. customto rise to 20° C.
  2. extractionwas extracted with diisopropyl oxide
  3. extractionThe combined organic phases were extracted with 100 ml of aqueous N sodium hydroxide
  4. extractionthe aqueous extract
  5. stirringwas stirred at 5° C. with a mixture of diisopropyl oxide and monosodium phosphate
  6. additionThe mixture was diluted with water
  7. extractionthe decanted aqueous phase was extracted with diisopropyl oxide
  8. customThe organic phase was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-bb651c228a7a46dd9a324843482d2b33
Source dataset
uspto-grants-1985_08
Patent number
US04537897

Reaction notes

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