Diethyl Ether → HCID 54424208, compound

HRID 1730114Notes

Reaction equation

HRID 1730114 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOCC.C([Li])CCC.[CH3:30][C:31]12[CH2:40][CH2:39][CH:34]([CH2:35][CH:36]1[CH:37]=O)[C:33]([CH3:42])([CH3:41])[C:32]2=[O:43].[CH2:44](Cl)[Cl:45]>O>[CH3:30][C:31]12[CH2:40][CH2:39][CH:34]([CH2:35][CH:36]1[CH:37]=[CH:44][Cl:45])[C:33]([CH3:42])([CH3:41])[C:32]2=[O:43]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 14682245HCID 14682245, compoundHCID 178418339Butyllithium

Product 1

HCID 54424208HCID 54424208, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 30 g of triphenylphosphine, 200 ml of anhydrous ether and 11 g of methylene chloride is cooled to -30° and 77 ml of 1.3M n-butyl lithium solution is added over one hour. To the stirred solution is added 11 g of crude 1,3,3-trimethyl-bicyclo-(2.2.2)-octan-2-one-6-carboxaldehyde. The mixture is slowly heated to reflux and held at reflux for 2 hours. The mixture is poured into 100 ml of water and the organic layer is separated and dried over Mg 804 and the solvent is stripped off the product. Structure: ##SPC43##

Workup

  1. temperatureis cooled to -30°
  2. temperatureThe mixture is slowly heated
  3. temperatureto reflux
  4. temperatureat reflux for 2 hours
  5. customthe organic layer is separated
  6. dry with materialdried over Mg 804

Sources & evidence

ORD record
ord-4163d56f098445f499a90a72b7caff0f
Source dataset
uspto-grants-1976_11
Patent number
US03991123

Reaction notes

Loading…