Propyltriphenylphosphonium bromide → HCID 69650485, compound

HRID 1790889Notes

Reaction equation

HRID 1790889 reaction equation
[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CC.[CH2:24]([Li])[CH2:25][CH2:26][CH3:27].[CH3:29][C:30]1([C:35]2(C=O)[CH2:37][CH2:36]2)[O:34][CH2:33][CH2:32][O:31]1>C(OCC)C>[CH:24]([C:35]1([C:30]2([CH3:29])[O:34][CH2:33][CH2:32][O:31]2)[CH2:37][CH2:36]1)=[CH:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 80374Propyltriphenylphosphonium bromideHCID 143755571-(2-Methyl-1,3-dioxolan-2-YL)cyclopropane-1-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 69650485HCID 69650485, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

7.2 g of propyltriphenylphosphonium bromide is dissolved in 100 ml of diethyl ether, and 7.5 ml of n-butyllithium solution (2.5 M in hexane) is added in drops under nitrogen at room temperature. It is stirred for 1 hour, and then 2.34 g of aldehyde 7 is added to 10 ml of diethyl ether. It is stirred for 1 more hour, quenched with sodium chloride solution, extracted with ethyl acetate, washed with sodium chloride solution, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 1.8 g of title substance 197 is obtained as a colorless oil (1:3 E,Z-mixture that cannot be separated).

Workup

  1. stirringIt is stirred for 1 more hour
  2. customquenched with sodium chloride solution
  3. extractionextracted with ethyl acetate
  4. washwashed with sodium chloride solution
  5. customdried on sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customThe residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 1.8 g of title substance 197
  8. customis obtained as a colorless oil (1:3 E,Z-mixture that cannot be separated)

Sources & evidence

ORD record
ord-3dff8306754042b4ab9952d4825cd9e0
Source dataset
uspto-grants-2006_07
Patent number
US07071344B1

Reaction notes

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