2,6-Lutidine → 5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate
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].O[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[CH2:22][CH2:21][CH2:20]2.N1C(C)=CC=CC=1C>ClCCl>[O:27]=[C:23]1[CH2:22][CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:26]=[CH:25][C:24]1=2Participants
5
Conditions
- Temperature
- 0 °C
Procedure
Trifluoromethanesulfonic anhydride (1.7 mL, 10 mmol) was added slowly over 1 hour to a solution of 6-hydroxy-1-tetralone (1.62 g, 10 mmol) and 2,6-lutidine (1.28 mL, 10 mmol) in dry dichloromethane (10 mL) cooled to 0° C. After 1 hour the solution was diluted with dichloromethane (10 mL) and washed with 1 M hydrochloric acid (20 mL). The organic layer was re-extracted with dichloromethane (50 mL) and the combined organics washed with 1 M hydrochloric acid (10 mL). The organics were dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography (Silica gel, CH2Cl2) to provide 2.7 g of compound 2 (93%).
Workup
- washwashed with 1 M hydrochloric acid (20 mL)
- extractionThe organic layer was re-extracted with dichloromethane (50 mL)
- washthe combined organics washed with 1 M hydrochloric acid (10 mL)
- dry with materialThe organics were dried over magnesium sulfate
- concentrationconcentrated under vacuum
- customThe residue was purified by column chromatography (Silica gel, CH2Cl2)
Sources & evidence
- ORD record
- ord-f957ca0c380b47baae40ea068da4305e
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173710B2
Reaction notes
Loading…