Bis(2-chloroethyl) ether → 2-(Tert-butyl-dimethyl-silanyloxy)-5-morpholin-4-yl-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].Cl[CH2:21][CH2:22][O:23][CH2:24][CH2:25]Cl.C(N(C(C)C)CC)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:7]=[CH:6][C:5]=1[O:11][Si:12]([C:15]([CH3:16])([CH3:18])[CH3:17])([CH3:13])[CH3:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5-amino-2-(tert-butyl-dimethyl-silanyloxy)benzoic acid methyl ester (4.5 g, 16 mmol), 2-chloroethyl ether (1.9 mL, 16.2 mmol), and diisopropylethylamine (5.6 mL, 32.1 mmol) in DMF (50 mL) was stirred at 100° C. for 48 h. The reaction mixture was poured into 10% aqueous NaHCO3 (100 mL) and extracted with ether (200 mL). The organic layer was washed with water (5×100 mL) and brine (100 mL), dried over magnesium sulfate (MgSO4), and concentrated to a red syrup. The residue was purified by flash chromatography (silica gel, 4×15 cm, eluted with 9/1 hexanes/EtOAc) to yield 2-(tert-butyl-dimethyl-silanyloxy)-5-morpholin-4-yl-benzoic acid methyl ester (1.0 g, 18%).
Workup
- extractionextracted with ether (200 mL)
- washThe organic layer was washed with water (5×100 mL) and brine (100 mL)
- dry with materialdried over magnesium sulfate (MgSO4)
- concentrationconcentrated to a red syrup
- customThe residue was purified by flash chromatography (silica gel, 4×15 cm, eluted with 9/1 hexanes/EtOAc)
Sources & evidence
- ORD record
- ord-89bc6f6a987b4e258aba964f24c71399
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242115B2
Reaction notes
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