1H-1,2,4-Triazole → HCID 22163230, compound

HRID 1199883Notes

Reaction equation

HRID 1199883 reaction equation
[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]2([C:12]([CH3:16])([CH3:15])[CH:13]=[CH2:14])[CH2:11][O:10]2)=[CH:3][CH:2]=1.[Na].[NH:24]1[CH:28]=[N:27][CH:26]=[N:25]1>C(O)CC>[C:1]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]([OH:10])([CH2:11][N:27]2[CH:26]=[N:25][N:24]=[CH:28]2)[C:12]([CH3:16])([CH3:15])[CH:13]=[CH2:14])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 5360545SodiumHCID 13254742HCID 13254742, compound

Product 1

HCID 22163230HCID 22163230, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

35.3 g (0.120 mol) of 2-(biphenyl-4-yloxymethyl)-2-(3,3-dimethylprop-1-en-3-yl)-oxirane, dissolved in 80 ml of n-propanol, were added to a boiling solution of 1 g (0.012 mol) of sodium propylate and 9.1 g (0.132 mol) of 1,2,4-triazole in 50 ml of n-propanol. After the solution had been boiled under reflux for two days, it was evaporated down under reduced pressure, the oily residue was taken up in 200 ml of ethyl acetate, and the solution was washed with three times 50 ml of water. After the organic phase had been dried over anhydrous sodium sulphate, the solution was concentrated under reduced pressure. After the residue had been triturated with 150 ml of ethyl acetate, 6.6 g (15.1% of theory) of 4-(biphenyl-4-yloxymethyl)-3,3-dimethyl-4-hydroxy-5-(1,2,4-triazol-4-yl)-pent-1-ene were obtained as colorless crystals of melting point 171° to 173° C. The oil (37.1 g) which remained after the filtrate had been evaporated down was taken up in 200 ml of acetone, and a solution of 34.6 g of naphthalene-1,5-disulphonic acid in 100 ml of acetone was added. The salt which crystallized out was filtered off under suction, washed with acetone, and taken up in a mixture of 250 ml of water and 250 ml of dichloromethane. The solution was rendered alkaline by stirring in 10% strength sodium carbonate solution. After the organic phase had been concentrated, 24 g of an oil were obtained, which was dissolved in ethyl acetate and the solution then filtered over silica gel. After the filtrate had been concentrated, 17.8 g (40.8% of theory) of 4-(biphenyl-4-yloxymethyl)-3,3-dimethyl-4-hydroxy-5-(1,2,4-triazol-1-yl)-pent-1-ene were obtained in the form of colorless crystals of melting point 85° to 87° C.

Workup

  1. temperatureunder reflux for two days
  2. customit was evaporated down under reduced pressure
  3. washthe solution was washed with three times 50 ml of water
  4. dry with materialAfter the organic phase had been dried over anhydrous sodium sulphate
  5. concentrationthe solution was concentrated under reduced pressure
  6. customAfter the residue had been triturated with 150 ml of ethyl acetate

Sources & evidence

ORD record
ord-d8645ce475d54980ae1fea7226c249dc
Source dataset
uspto-grants-1990_02
Patent number
US04904296

Reaction notes

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