Water → 1-(5-Methyl-1,3-dioxan-5-yl)-1-allyloxy-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propane

HRID 851625Notes

Reaction equation

HRID 851625 reaction equation
[CH3:1][C:2]1([CH:8]([OH:23])[CH:9]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:7][O:6][CH2:5][O:4][CH2:3]1.[H-].[Na+].[CH2:26](Br)[CH:27]=[CH2:28].O>O1CCCC1>[CH3:1][C:2]1([CH:8]([O:23][CH2:28][CH:27]=[CH2:26])[CH:9]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH2:10][C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[CH2:3][O:4][CH2:5][O:6][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 128556541-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propan-1-ol

Product 1

HCID 128556561-(5-Methyl-1,3-dioxan-5-yl)-1-allyloxy-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propaneYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
25 °C

Procedure

A solution of 23.6 g (0.07 mole) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propan-1-ol in 100 ml of tetrahydrofuran is added dropwise to a suspension of 2.4 g of sodium hydride in 120 ml of dry tetrahydrofuran. After stirring the mixture for 12 hours at 25° C, a solution of 9.7 g (0.08 mole) of allyl bromide in 20 ml of tetrahydrofuran is added dropwise. The reaction mixture is stirred for 36 hours, 20 ml of water are then added cautiously, and the batch is evaporated down. The residue is taken up in 350 ml of methylene chloride, the solution is washed with three times 100 ml of water, and the organic phase is dried and evaporated down. The residue is mixed with 30 ml of petroleum ether and 10 ml of ether and left to stand overnight at +3° C. The crystalline, colorless precipitate is filtered off, washed with petroleum ether and dried. 22.6 g (87.5%) of 1-(5-methyl-1,3-dioxan-5-yl)-1-allyloxy-2-(1,2,4-triazol-1-yl)-3-(4-chlorophenyl)-propane, of melting point 113°-115° C., are obtained.

Workup

  1. stirringThe reaction mixture is stirred for 36 hours
  2. customthe batch is evaporated down
  3. washthe solution is washed with three times 100 ml of water
  4. customthe organic phase is dried
  5. customevaporated down
  6. additionThe residue is mixed with 30 ml of petroleum ether and 10 ml of ether
  7. waitleft
  8. waitto stand overnight at +3° C
  9. filtrationThe crystalline, colorless precipitate is filtered off
  10. washwashed with petroleum ether
  11. customdried

Sources & evidence

ORD record
ord-977114a690f24c51bc910058918fbb54
Source dataset
uspto-grants-1983_05
Patent number
US04385925

Reaction notes

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