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

HRID 352610Notes

Reaction equation

HRID 352610 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-235df0ba5990445ebd4c97bf914d2a64
Source dataset
uspto-grants-2004_06
Patent number
US06747054B2

Reaction notes

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