Hydrochloric Acid → HCID 15315836, compound

HRID 353417Notes

Reaction equation

HRID 353417 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: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][C:21](=[O:26])[CH2:22]1)(=[O:20])[O:17][CH2:18][CH3:19])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 135882-Cyclopenten-1-oneHCID 65367Trimethylsilyl triflateHCID 3780918Diethylphosphite

Product 1

HCID 15315836HCID 15315836, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.52 mmol trimethylsilyltriflate are added dropwise to 11.4 mmol diethylphosphite and 12.4 mmol N,O-bis-(trimethylsilyl)acetamid in 5 ml dichlormethane at 0° C. After 30 minutes of stirring 0.52 mmol 2-cyclopenten-1-one are added dropwise thereto at the same temperature and stirring is continued for 1 h. The enolsilane intermediate product is hydrolized by 3 ml 1 n HCl and 3 hours of stirring. The organic phase is separated, dried over magnesiumsulfate and concentrated. The raw product may be chromatographed on SiO2 and, after concentrating the desired fractions, results to 3-(phosphonic acid diethylester)-cyclopentan-1-one (a) with boiling point0.25 Torr=104° C. in a good 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 may be chromatographed on SiO2
  7. concentrationafter concentrating the desired fractions

Sources & evidence

ORD record
ord-76a7688b28e34de48d9b84dbe196c58b
Source dataset
uspto-grants-2004_06
Patent number
US06753324B2

Reaction notes

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