Tetrahydrofuran → 4-(1,1-Dimethyl-4,4,4-trifluoro-2-butynyl)anisole
Reaction equation
[Li][CH2:2]CCC.[F:6][C:7]([F:13])([F:12])S([O-])(=O)=O.FC(F)(F)[S+]1[C:20]2C=C[CH:23]=[CH:24][C:19]=2[C:18]2[CH:25]=[CH:26][CH:27]=[CH:28][C:17]1=2.C1C[O:34][CH2:33]C1>>[CH3:2][C:19]([C:18]1[CH:17]=[CH:28][C:27]([O:34][CH3:33])=[CH:26][CH:25]=1)([CH3:20])[C:24]#[C:23][C:7]([F:13])([F:12])[F:6]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of Compound 56 (0.22 g, 1.26 mmol) in THF (8 ml) was added n-BuLi (1.69 M in hexane, 0.82 ml, 1.39 mmol) at −78° C. under N2, then warmed up to 0° C., and stirred for 1 h. S-(Trifluoromethyl)dibenzothiophenium trifluoromethane-sulfonate (1.01 g, 2.52 mmol) was added, and stirred for 3 h at 0° C. The mixture was quenched by the addition of NaHCO3 aq., and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated. This was purified by SiO2 chromatography to give Compound 57 (38 mg, 13%) as a colorless oil.
Workup
- stirringstirred for 3 h at 0° C
- customThe mixture was quenched by the addition of NaHCO3 aq.
- extractionextracted with CH2Cl2
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThis was purified by SiO2 chromatography
Sources & evidence
- ORD record
- ord-65b09b873966426fb341b59ac38de3fc
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06329396B1
Reaction notes
Loading…