Hexane → HCID 20203945, compound

HRID 977903Notes

Reaction equation

HRID 977903 reaction equation
[CH3:1][CH2:2][CH2:3]CCC.C([Li])CCC.[CH:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:24][C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:22][C:20](=O)[CH:19]=2)=[CH:14][CH:13]=1.[Cl:31]([OH:35])(=[O:34])(=[O:33])=[O:32]>O1CCCC1>[Cl:31]([O-:35])(=[O:34])(=[O:33])=[O:32].[C:15]1([C:18]2[C:19]([CH2:1][CH2:2][CH3:3])=[CH:20][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O+:24]=2)[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 24247Perchloric AcidHCID 2832272,6-Diphenyl-4H-pyran-4-oneHCID 178418339Butyllithium

Product 1

HCID 20203945HCID 20203945, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A 1.7M hexane solution (3.5 ml) containing 6 mmol of n-butyl lithium was added dropwise to 10 ml of an anhydrous tetrahydrofuran solution containing 1.24 g (5 mmol) of 2,6-diphenyl-γ-pyrone which was cooled to -20° C. One hour later, the reaction mixture was poured into 50 ml of a 6 wt% aqueous solution of perchloric acid. The precipitated solid was collected by filtration, dissolved in a small amount of methylene chloride and reprecipitated in diethyl ether. The precipitated yellow solid was separated by filtration and dried to obtain 0.88 g (yield: 45%) of 2,6-diphenyl-3-n-propylpyrylium perchlorate.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. dissolutiondissolved in a small amount of methylene chloride
  3. customreprecipitated in diethyl ether
  4. customThe precipitated yellow solid was separated by filtration
  5. customdried

Sources & evidence

ORD record
ord-7db78350b34b4156acf78f2663d9a7ad
Source dataset
uspto-grants-1987_05
Patent number
US04663260

Reaction notes

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