Sodium Iodide → (Rac)-4-(tert-butyl-dimethyl-silanyloxy)-2-iodo-butyric acid methyl ester

HRID 655487Notes

Reaction equation

HRID 655487 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@@H:4](OS(C)(=O)=O)[CH2:5][CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[I-:21].[Na+]>CC(=O)CC>[CH3:1][O:2][C:3](=[O:20])[CH:4]([I:21])[CH2:5][CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86638104(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-butyric acid methyl ester

Product 1

HCID 87149689(Rac)-4-(tert-butyl-dimethyl-silanyloxy)-2-iodo-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2.89 g (8.85 mmol) of (S)-4-(tert-butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-butyric acid methyl ester in 90 ml of 2-butanone was treated with 2.65 g (17.70 mmol) of sodium iodide and stirred at 90° C. for 1¼ h. The reaction was cooled, filtered and evaporated. The residue was suspended in dichloromethane treated with Na2SO4 and filtered to give after evaporation 2.94 g (93%) of the title compound as dark brown oil. MS: 343.0 (M-CH3)+.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customevaporated
  4. additiontreated with Na2SO4
  5. filtrationfiltered
  6. customto give
  7. customafter evaporation 2.94 g (93%) of the title compound as dark brown oil

Sources & evidence

ORD record
ord-0cd797abab3244b9a40efce93b8b3412
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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