Diethyl (3-oxobutyl)phosphonate → Diethyl 3-hydroxy-3-methyl-3-(1-methyl-1,2,4-triazol-5-yl)propyl-phosphonate

HRID 6337Notes

Reaction equation

HRID 6337 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][CH:4]=[N:3]1.[O:7]=[C:8]([CH3:19])[CH2:9][CH2:10][P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]>O1CCCC1>[OH:7][C:8]([CH3:19])([C:6]1[N:2]([CH3:1])[N:3]=[CH:4][N:5]=1)[CH2:9][CH2:10][P:11](=[O:18])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 14033Diethyl (3-oxobutyl)phosphonateHCID 224591H-1,2,4-Triazole, 1-methyl-

Product 1

HCID 19793143Diethyl 3-hydroxy-3-methyl-3-(1-methyl-1,2,4-triazol-5-yl)propyl-phosphonateYield 28.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-1,2,4-triazole (3.0 g, 36.1 mmol) in tetrahydrofurane (60 ml) was added n-buthyllithium (43.3 mmol, 1.2 eq) at -78° C. under nitrogen. The mixture was stirred for 1 hour, then diethyl 3-oxo-butylphosphonate (8.3 g, 39.7 mmol, 1.1 eq) was added. The mixture was stirred for 2 hours and quenched with aq. NH4Cl (ca. 15 ml). The mixture was warmed to room temperature and extracted with CH2Cl2 (5×100 ml). The extract was dried over MgSO4, concentrated in vacuo, and purified by a silica gel column chromatography (200 g, AcOEt-EtOH) to give (2.99 g, 28% yield) of diethyl 3-hydroxy-3-methyl-3-(1-methyl-1,2,4-triazol-5-yl)propyl-phosphonate.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. customquenched with aq. NH4Cl (ca. 15 ml)
  3. extractionextracted with CH2Cl2 (5×100 ml)
  4. dry with materialThe extract was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified by a silica gel column chromatography (200 g, AcOEt-EtOH)

Sources & evidence

ORD record
ord-722703b0bdef43369d32d6d5d22467c1
Source dataset
uspto-grants-1993_09
Patent number
US05248655

Reaction notes

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