Neopentyl alcohol → 2,2-Dimethylpropyl trifluoromethanesulfonate

HRID 20411

Reaction equation

HRID 20411 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH2:16](O)[C:17]([CH3:20])([CH3:19])[CH3:18].N1C(C)=CC=CC=1C>ClCCl>[CH3:16][C:17]([CH3:20])([CH3:19])[CH2:18][O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 6404Neopentyl alcoholHCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 156962812,2-Dimethylpropyl trifluoromethanesulfonateYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoromethanesulphonic anhydride (1.12 mL, 6.8 mmol) to a solution of neopentylalcohol (0.5 g, 5.7 mmol) and 2,6-lutidine (0.7 mL, 6.8 mmol) in dichloromethane (10 mL) at −78° C. and stir for 1 hour. Add water to quench the reaction, separate the organic layer and extract the aqueous layer with dichloromethane. Combine the organic layers, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 1:4 hexane:dichloromethane) to give the desired compound as an oil (0.9 g, 72% yield).

Workup

  1. customAdd water to quench
  2. customthe reaction
  3. customseparate the organic layer
  4. extractionextract the aqueous layer with dichloromethane
  5. dry with materialdry (magnesium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 1:4 hexane:dichloromethane)

Sources & evidence

ORD record
ord-6975154842644f7fbddb9e327f2bcaee
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

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