Hydrochloric Acid → HCID 15315828, compound

HRID 353418Notes

Reaction equation

HRID 353418 reaction equation
C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[CH2:13]([O:15][P:16]([O-:20])[O:17][CH2:18][CH3:19])[CH3:14].[C:21]1(=[O:27])[CH2:26][CH2:25][CH2:24][CH:23]=[CH:22]1.Cl>ClCCl>[CH2:13]([O:15][P:16]([CH:23]1[CH2:24][CH2:25][CH2:26][C:21](=[O:27])[CH2:22]1)(=[O:20])[O:17][CH2:18][CH3:19])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 135942-Cyclohexen-1-oneHCID 65367Trimethylsilyl triflateHCID 3780918Diethylphosphite

Product 1

HCID 15315828HCID 15315828, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.52 mmol trimethylsilyltriflate is added dropwise to 11.4 mmol diethylphosphite and 12.4 mmol N,O-bis-(trimethylsilyl)acetamide in 5 ml dichlormethane at 0° C. After 30 minutes of stirring at the same temperature 0.52 mmol 2-cyclohexen-1-one are added dropwise thereto and is stirred for 1 h. The enolsilane intermediate product is hydrolized by 3 ml 1 n HCl during 3 hours of stirring. The organic phase is separated, dried over magnesiumsulfate and concentrated. The raw product can be chromatographed on SiO2 and after concentration of the desired fractions results in 3-oxo-cyclohexylphosphonic acid diethylester 2(a) in a 95% yield.

Workup

  1. additionare added dropwise
  2. stirringof stirring
  3. customThe organic phase is separated
  4. dry with materialdried over magnesiumsulfate
  5. concentrationconcentrated
  6. customThe raw product can be chromatographed on SiO2
  7. customafter concentration of the desired fractions results in 3-oxo-cyclohexylphosphonic acid diethylester 2(a) in a 95% yield

Sources & evidence

ORD record
ord-884ec04ad3304fed892541bf755c009a
Source dataset
uspto-grants-2004_06
Patent number
US06753324B2

Reaction notes

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