2,6-Lutidine → 2-((tert-Butyldimethylsilyl)oxy)ethyl trifluoromethanesulfonate

HRID 597899Notes

Reaction equation

HRID 597899 reaction equation
[Si:1]([CH:8](O)CO)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])C.CC1C=CC=[C:15]([CH3:19])N=1.[F:20][C:21]([F:34])([F:33])[S:22]([O:25]S(C(F)(F)F)(=O)=O)(=[O:24])=[O:23].[O-:35]S(C(F)(F)F)(=O)=O>ClCCl>[O:25]([CH2:15][CH2:19][O:35][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:8])[S:22]([C:21]([F:34])([F:33])[F:20])(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 2758875Trifluoromethanesulfonate2×HCID 136812512-(Tert-butyldimethylsilyl)-ethylene glycol

Product 1

HCID 156781072-((tert-Butyldimethylsilyl)oxy)ethyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(tert-butyldimethylsilyl)-ethylene glycol (125 mg, 0.71 mmol) and 2,6-lutidene (0.08 mL, 0.69 mmol) in 6 mL dichloromethane was cooled to −78° C. Trifluoromethanesulfonic anhydride (0.11 mL, 0.65 mmol) was added over a period of 5 min and stirring was continued for additional 15 min at −78° C. to complete the formation of the triflate. The triflate was used in situ for the reaction as described in 3.2 below.

Sources & evidence

ORD record
ord-0871dd79b7244323abdfeb90e4cf57c8
Source dataset
uspto-grants-2011_03
Patent number
US07897608B2

Reaction notes

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