Solketal → 2,2-Dimethyl-4-(trifluoromethylsulfonyloxymethyl)-1,3-dioxolane
Reaction equation
[F:1][C:2]([S:5]([O:8]S(C(F)(F)F)(=O)=O)(=[O:7])=[O:6])([F:4])[F:3].[CH3:16][C:17]1([CH3:24])[O:21][CH:20]([CH2:22]O)[CH2:19][O:18]1.N1C(C)=CC=CC=1C>C(Cl)Cl.O>[F:1][C:2]([F:4])([F:3])[S:5]([O:8][CH2:22][CH:20]1[CH2:19][O:18][C:17]([CH3:24])([CH3:16])[O:21]1)(=[O:7])=[O:6]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
Trifluoromethylsulfonic anhydride (7.03 ml, 41.6 mmol) was added dropwise over 15 mins to a solution of solketal (4.70 ml, 37.8 mmol) and 2,6-lutidine (5.73 ml, 49.2 mmol) in DCM (126 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour. The mixture was diluted with DCM (100 mL) and water (100 mL), the phases were separated and the aqueous phase extracted with DCM (3×50 mL). The combined organic extracts were dried over sodium sulfate and evaporated under vacuum to afford the title compound as a crude material which was used directly.
Workup
- customthe phases were separated
- extractionthe aqueous phase extracted with DCM (3×50 mL)
- dry with materialThe combined organic extracts were dried over sodium sulfate
- customevaporated under vacuum
Sources & evidence
- ORD record
- ord-a49eebb5cf8949608cdf7b008990bf72
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359381B2
Reaction notes
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