2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 3-[3,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]tetrahydro-2H-pyran
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([F:15])[CH:14]=1)[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][O:8][CH2:7]1.[Li]CCCC.C(O[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([F:15])[C:14]=1[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)[O:5][CH:6]1[CH2:11][CH2:10][CH2:9][O:8][CH2:7]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 3-(3,5-difluorophenoxy)tetrahydro-2H-pyran (1.42 g, 6.63 mmol) in THF (26 mL) at −78° C., a solution of n-BuLi in hexanes (1.6 M; 10.4 mL, 16.6 mmol) was added slowly through a dripping funnel. When addition was complete, the mixture was kept at −78° C. for 1 h. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.06 mL, 19.9 mmol) was then added in one portion. The mixture was allowed to warm to room temperature and stirred for 1 h. The mixture was quenched with NaHCO3 solution and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give sub-title compound as a colorless oil. LCMS calc. for C17H24BF2O4 (M+H)+ m/z=341.2. found: 341.1.
Workup
- additionWhen addition
- customThe mixture was quenched with NaHCO3 solution
- extractionextracted with EtOAc
- extractionThe organic extract
- washwas washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-8b43a5378ca34d4eb56e6c43ece6ad08
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09200004B2
Reaction notes
Loading…