Triacetoxyperiodinane → [3-(4-Fluoro-3-methyl-phenyl)-2-oxo-propyl]-phosphonic acid diethyl ester

HRID 1267459Notes

Reaction equation

HRID 1267459 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH:10]([OH:20])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([CH3:19])[CH:13]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([O:3][P:4]([CH2:9][C:10](=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([CH3:19])[CH:13]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86585241[3-(4-Fluoro-3-methyl-phenyl)-2-hydroxy-propyl]-phosphonic acid diethyl ester

Product 1

HCID 86585242[3-(4-Fluoro-3-methyl-phenyl)-2-oxo-propyl]-phosphonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [3-(4-fluoro-3-methyl-phenyl)-2-hydroxy-propyl]-phosphonic acid diethyl ester (1.37 g, 4.51 mmol) in CH2Cl2 (30 mL) was added Dess-Martin reagent (Chemical Abstracts No. 87413-04-0, 2.10 g, 4.96 mmol). The reaction mixture was stirred at room temperature for 2 h and additional CH2Cl2 was added. The organic solution was washed with NaHCO3 (2 times) and once with brine. The organic solution was dried (MgSO4), filtered and concentrated. Purification by medium pressure chromatography (20% EtOAc in hexanes to 70% EtOAc in hexanes) provided the title compound of Preparation 6 (1.1 g).

Workup

  1. washThe organic solution was washed with NaHCO3 (2 times) and once with brine
  2. dry with materialThe organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by medium pressure chromatography (20% EtOAc in hexanes to 70% EtOAc in hexanes)
  6. customprovided

Sources & evidence

ORD record
ord-77a9127a366c400d97d3503e4424ff52
Source dataset
uspto-grants-2003_04
Patent number
US06552067B2

Reaction notes

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