tert-Butyldimethylsilyl trifluoromethanesulphonate → HCID 53920169, compound

HRID 1265398Notes

Reaction equation

HRID 1265398 reaction equation
[Si:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:16]([O-:19])(O)=[O:17].[Na+]>N1C=CC=CC=1.CCCCCC>[C:4]([Si:1]([CH3:3])([CH3:2])[O:19][C:16]([O:8][Si:1]([CH3:3])([CH3:2])[C:4]([CH3:7])([CH3:6])[CH3:5])=[O:17])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium Bicarbonate

Product 1

HCID 53920169HCID 53920169, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of triethylsilyloxy keto diol 6 (883 mg, 2.31 mmol) in 35 mL of pyridine under nitrogen at 0° C. was added dropwise 0.485 mL (2.771 mmol) of TBSOTf. The solution was then warmed to room temperature. After 2 h at room temperature, the solution was diluted with 100 mL of hexane and poured into 150 mL of a saturated aqueous NaHCO3 solution. The organic layer was separated, and the aqueous layer was extracted with two 100 mL portions of hexane. The organic layers were combined, and washed with 50 mL of a 10% aqueous CuSO4 solution followed by 20 mL of H2O, and dried over anhydrous Na2SO4. Removal of the solvent followed by flash chromatography purification (2.5% EtOAc/hexane) to give 1.122 g of t-butyldimethylsilyloxy ketone 7 (98% yield) as a white solid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with two 100 mL portions of hexane
  3. washwashed with 50 mL of a 10% aqueous CuSO4 solution
  4. dry with materialdried over anhydrous Na2SO4
  5. customRemoval of the solvent
  6. customfollowed by flash chromatography purification (2.5% EtOAc/hexane)

Sources & evidence

ORD record
ord-fd180673fd5444cebd106fe330a3a747
Source dataset
uspto-grants-2003_04
Patent number
US06545168B1

Reaction notes

Loading…