Reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[Si]([O:19][CH2:20][CH2:21][O:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1)(C(C)(C)C)(C)C.C([O-])(O)=O.[Na+]>CO>[S:24]1[CH:25]=[CH:26][N:27]=[C:23]1[O:22][CH2:21][CH2:20][OH:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
para-Toluenesulfonic acid (11.2 g, 58.0 mmol) was added to a sol. of 2-[2-(tert-butyldimethylsilanyloxy)ethoxy]thiazole (15.0 g, 58.0 mmol) in MeOH (300 mL) at 0° C. The mixture was stirred for 2 h at 0° C. Aq. sat. NaHCO3 was added until a pH of 6-7 was reached. The solvents were partially removed under reduced pressure, and the residue was diluted with EtOAc. The mixture was washed with aq. sat. NaHCO3 (1×), and the aq. phase was extracted back with EtOAc (1×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:1) yielded the title compound (5.43 g, 65%). LC-MS: tR=0.48 min, ES+: 146.09.
Workup
- customThe solvents were partially removed under reduced pressure
- additionthe residue was diluted with EtOAc
- washThe mixture was washed with aq. sat. NaHCO3 (1×)
- extractionthe aq. phase was extracted back with EtOAc (1×)
- dry with materialextracts were dried over MgSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
- customPurification of the crude by FC (EtOAc/heptane 1:1)
Sources & evidence
- ORD record
- ord-9f15072f02ab48f599a29b040cd8b7e1
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138340B2
Linked notes
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