Water → 3,4-dihydro-2H-chromen-2-ylmethyl 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:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH:17]1[CH2:26]O.N1C=CC=CC=1.O>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][CH2:26][CH:17]1[CH2:18][CH2:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:16]1)(=[O:5])=[O:4]Participants
Conditions
- Temperature
- -5 °C
Procedure
Trifluoromethanesulfonic anhydride (19.6 g, 69.5 mmol) in DCM (15 mL) was added to a solution of the title compound from Step 1 (9.50 g, 57.9 mmol) in DCM (100 mL) and pyridine (11.0 g, 139 mmol) cooled to −5° C. The reaction was then stirred at 0° C. for 1 h. Water (150 mL) was added and the reaction was extracted with DCM (150 mL). The organic layer was washed with 1 M HCl (180 mL), water (100 mL), and NaHCO3 aqueous solution (100 mL). The organic phase was dried over Na2SO4, filtered and concentrated to give the title compound (13.5 g, 79%) as a pale-brown oil. 1H NMR (400 MHz, CDCl3): δ 7.12-7.04 (m, 2H), 6.90-6.83 (m, 2H), 4.66-4.61 (m, 2H), 4.36-4.31 (m, 1H), 2.96-2.79 (m, 2H), 2.09-2.03 (m, 1H), 1.95-1.84 (m, 1H). LCMS: 314 (M+NH4)+
Workup
- extractionthe reaction was extracted with DCM (150 mL)
- washThe organic layer was washed with 1 M HCl (180 mL), water (100 mL), and NaHCO3 aqueous solution (100 mL)
- dry with materialThe organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-55bbe18dd1f24041b278091f932034d1
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115114B2
Reaction notes
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