Methanol → 3-Hydroxy-3-methyl-3-(1-methyl-1,2,4-triazol-5-yl)propyl-phosphonic acid

HRID 6338

Reaction equation

HRID 6338 reaction equation
[OH:1][C:2]([CH3:19])([C:13]1[N:17]([CH3:18])[N:16]=[CH:15][N:14]=1)[CH2:3][CH2:4][P:5](=[O:12])([O:9]CC)[O:6]CC.C[Si](Br)(C)C.CO.C1OC1C>C(Cl)Cl.C(OCC)C>[OH:1][C:2]([CH3:19])([C:13]1[N:17]([CH3:18])[N:16]=[CH:15][N:14]=1)[CH2:3][CH2:4][P:5](=[O:6])([OH:12])[OH:9]

Participants

7

Reactant 4

HCID 887MethanolHCID 6378Propylene OxideHCID 76113BromotrimethylsilaneHCID 19793143Diethyl 3-hydroxy-3-methyl-3-(1-methyl-1,2,4-triazol-5-yl)propyl-phosphonate

Product 1

HCID 197931443-Hydroxy-3-methyl-3-(1-methyl-1,2,4-triazol-5-yl)propyl-phosphonic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 3-hydroxy-3-methyl-3-(1-methyl-1,2,4-triazol-5-yl)propylphosphonate (1.2 g, 4.12 mmol) in CH2Cl2 (24 ml) was added TMSBr (2.72 ml, 20.6 mmol, 5 eq) at room temperature under nitrogen. The reaction mixture was stirred for 16 hours. Then methanol (12 ml) was added to the mixture. After stirring for 2 hours, addition of propylene oxide (2.4 ml) and dilution with diethylether gave colourless precipitates which were collected on a glass filter under nitrogen, washed with diethylether, and dried in vacuo to give pure 3-hydroxy-3-methyl-3-(1-methyl-1,2,4-triazol-5-yl)propyl-phosphonic acid, compound no 5.001 (0,63 g, 65% yield). ##STR49##

Workup

  1. stirringAfter stirring for 2 hours
  2. customgave colourless
  3. customprecipitates which
  4. customwere collected on a glass
  5. filtrationfilter under nitrogen
  6. washwashed with diethylether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3ce26230d98c428aa71701a3a4059bb1
Source dataset
uspto-grants-1993_09
Patent number
US05248655

Linked notes

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