Dimethyl methylphosphonate → Dimethyl 2-oxo-2-(1-adamantyl)-ethylphosphonate

HRID 435122Notes

Reaction equation

HRID 435122 reaction equation
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])CCC.[C:13]12([C:23](Cl)=[O:24])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2>O.C1COCC1.CCCCCC>[O:24]=[C:23]([C:13]12[CH2:22][CH:17]3[CH2:16][CH:15]([CH2:21][CH:19]([CH2:18]3)[CH2:20]1)[CH2:14]2)[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]

Participants

7

Reactant 3

HCID 12958Dimethyl methylphosphonateHCID 989151-Adamantanecarbonyl chlorideHCID 178418339Butyllithium

Product 1

HCID 13186070Dimethyl 2-oxo-2-(1-adamantyl)-ethylphosphonate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a tetrahydrofuran (200 ml) solution of dimethyl methylphosphonate (20.2 g) was added a 1.6 M hexane solution of n-butyl lithium (100 ml) at -60° C. under nitrogen. To this mixture was added a THF solution of 1-adamantyl carboxylic acid chloride (30 g) and it was stirred at the same temperature for 5 hrs and at room temperature for 12 hrs. The mixture was diluted with water and extracted with diethyl ether. The extract was dried and concentrated in vacuo. After the residue was distilled off the volatile impurity (~200° C./0.6 mmHg), there was obtained dimethyl 2-oxo-2-(1-adamantyl)-ethylphosphonate as an oil.

Workup

  1. extractionextracted with diethyl ether
  2. customThe extract was dried
  3. concentrationconcentrated in vacuo
  4. distillationAfter the residue was distilled off the volatile impurity (~200° C./0.6 mmHg)

Sources & evidence

ORD record
ord-179483d259b14b63acb695f0b280f3cc
Source dataset
uspto-grants-1983_08
Patent number
US04400393

Reaction notes

Loading…