2,6-Lutidine → ((2-(Bromomethyl)benzyl)oxy)(tert-butyl)dimethylsilane
Reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][OH:10].N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])(=O)=O>C(Cl)Cl>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][O:10][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the title compound of step (A) (10 g, 50 mmol) in CH2Cl2 (80 ml) cooled at 0° C. was added 2,6-lutidine (7.57 mL, 65 mmol), followed by dropwise addition of tert-butyldimethylsilyl trifluoromethanesulfonate (14.92 mL, 65 mmol). The reaction mixture was stirred at 0° C. for 45 minutes, then quenched with H2O (20 mL) and partitioned between EtOAc (450 mL) and H2O (150 mL). The organic layer was separated and washed with 10% NaHCO3 solution, brine (2×), dried (MgSO4) and concentrated in vacuo to give a yellow syrup, which was chromatographed eluting with 10-50% EtOAc/hexane to afford 13.89 g (88%) of the title compound of this step as a light yellow oil.
Workup
- customquenched with H2O (20 mL)
- custompartitioned between EtOAc (450 mL) and H2O (150 mL)
- customThe organic layer was separated
- washwashed with 10% NaHCO3 solution, brine (2×)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customto give a yellow syrup, which
- customwas chromatographed
- washeluting with 10-50% EtOAc/hexane
Sources & evidence
- ORD record
- ord-b5bab3103598436ba6a3693aad2b8c5b
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235922B1
Reaction notes
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