Tetrahydrofuran → HCID 57188762, compound

HRID 638511Notes

Reaction equation

HRID 638511 reaction equation
C([CH:3]1[CH2:5][CH:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])=O.C(C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O.[O:33]1C[CH2:36][CH2:35][CH2:34]1>>[CH:4]1([C:6]([O:8][CH2:9][CH2:10][CH:36]=[CH:35][CH:34]=[O:33])=[O:7])[CH2:3][CH2:5]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 89334Ethyl 2-formylcyclopropanecarboxylate

Product 1

HCID 57188762HCID 57188762, compoundYield 80%

Procedure

A mixture of ethyl 2-formyl-1-cyclopropanecarboxylate (55 g, 0.39 moles) and formylmethylenetriphenylphosphorane (117.7 g, 0.39 moles) in tetrahydrofuran (600 ml) is refluxed for 40 hours. The solvent is removed under reduced pressure. The residue is triturated with ether/hexane (1:1) and filtered. The filtrate is evaporated, dissolved in ether/petroleum ether and filtered through a column of silica gel. The solvent is stripped from the filtrate to give a dark oil. The oil is distilled under reduced pressure to give the product as a clear colorless oil (52.1 g, 80%), b.p. 105°-113° C. (2.0 mm).

Workup

  1. temperatureis refluxed for 40 hours
  2. customThe solvent is removed under reduced pressure
  3. customThe residue is triturated with ether/hexane (1:1)
  4. filtrationfiltered
  5. customThe filtrate is evaporated
  6. dissolutiondissolved in ether/petroleum ether
  7. filtrationfiltered through a column of silica gel
  8. customto give a dark oil
  9. distillationThe oil is distilled under reduced pressure

Sources & evidence

ORD record
ord-cd8ef0a236d046238ba2f1cfd9b1f684
Source dataset
uspto-grants-1985_12
Patent number
US04562006

Reaction notes

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