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

HRID 2219713Notes

Reaction equation

HRID 2219713 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 (Dess-Martin periodinane, Aldrich Chemical Co., Milwaukee, Wis., 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-191e34f848f64ca28b4deda4ca043652
Source dataset
uspto-grants-2008_08
Patent number
US07414071B2

Reaction notes

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