Diethyl Ether → HCID 10942985, compound

HRID 486920Notes

Reaction equation

HRID 486920 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.CCOCC.[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)C.[CH:34]1[C:39]([CH:40]=O)=[CH:38][C:37]2[O:42][CH2:43][O:44][C:36]=2[CH:35]=1>CCCCCC>[O:44]1[C:36]2[CH:35]=[CH:34][C:39]([CH:40]=[C:2]([CH3:3])[CH3:1])=[CH:38][C:37]=2[O:42][CH2:43]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8438PiperonalHCID 2795292Isopropyltriphenylphosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 10942985HCID 10942985, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

62.5 ml of a 1.6M solution of butyllithium in hexane was added to 500 ml of anhydrous ether. 38.5 g of isopropyltriphenylphosphonium bromide was added thereto in a nitrogen gas stream and the mixture was stirred for 4 h. 18 g of piperonal was added to the reaction mixture and the resulting mixture was stirred for 5.5 h and then filtered. The filtrate was washed with 1 l of ether, concentrated under reduced pressure and purified according to silica gel column chromatography (hexane/ethyl acetate=10:1) to obtain 13.1 g of the intended compound in the form of a colorless oil.

Workup

  1. stirringthe resulting mixture was stirred for 5.5 h
  2. filtrationfiltered
  3. washThe filtrate was washed with 1 l of ether
  4. concentrationconcentrated under reduced pressure
  5. custompurified

Sources & evidence

ORD record
ord-90b35bba8cce4b5899d4c50f12b4af59
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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