Diethyl Ether → HCID 54445565, compound

HRID 274888Notes

Reaction equation

HRID 274888 reaction equation
O[C:2]([C:10]1[CH2:11][O:12][C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:15][CH:14]=2)([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].P(Cl)(Cl)(Cl)=O.C(OCC)C>C1(C)C=CC=CC=1>[C:20]1([C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[O:12][CH2:11][C:10]([C:2]([CH3:9])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:19]3)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24813Phosphorus oxychlorideHCID 20089256HCID 20089256, compound

Product 1

HCID 54445565HCID 54445565, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The whole of the solid obtained in Step C is dissolved in 70 ml of toluene and then treated with 1.25 ml (13.3 mmol) of phosphorus oxychloride. The mixture is refluxed for one hour. After returning to room temperature, the reaction mixture is poured onto 60 ml of ice-water and then mixed with 100 ml of diethyl ether. Customary treatment of the organic phase yields, after purification over a silica column (eluant: methylene chloride), 12.36 g of a yellow solid recrystallised from diisopropyl ether.

Workup

  1. temperatureThe mixture is refluxed for one hour
  2. customAfter returning to room temperature
  3. customCustomary treatment of the organic phase yields
  4. customafter purification over a silica column (eluant: methylene chloride), 12.36 g of a yellow solid
  5. customrecrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-d7e1ca914f004224946f81556a441e58
Source dataset
uspto-grants-1995_02
Patent number
US05391569

Reaction notes

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