Ethyl vinyl ether → 1-Ethoxyethyl ether
Reaction equation
C1(S(C(C(O)C(C)=CCCC(C)=CC(S(C2C=CC=CC=2)(=O)=O)CC=C(C)CCC=C(C)[CH:35]([OH:55])[CH:36](S(C2C=CC=CC=2)(=O)=O)C=C(C)CCC=C(C)C)C=C(C)CCC=C(C)C)(=O)=O)C=CC=CC=1.[CH:70]([O:72][CH2:73][CH3:74])=[CH2:71].C1(C)C=CC(S([O-])(=O)=[O:82])=CC=1.[NH+]1[CH:91]=[CH:90]C=CC=1>C(Cl)Cl>[CH2:70]([O:72][CH:73]([O:82][CH:90]([O:55][CH2:35][CH3:36])[CH3:91])[CH3:74])[CH3:71]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of the C40 diol compound (L) (1.00 g, 1.00 mmol) in CH2Cl2 (10 mL) at 0° C. were added ethyl vinyl ether (0.80 mL, 8.00 mmol) and pyridinium p-toluenesulfonate (0.13 g, 0.50 mmol). The mixture was stirred at 0° C. for 1 h, and warmed to and stirred at room temperature for 14 h. The mixture was then diluted with CH2Cl2 (30 mL), washed with saturated NaHCO3 (10 mL×3), dried over anhydrous K CO3, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel (deactivated by Et3N) column chromatography to give the bis(1-ethoxyethyl)ether (M-3) (1.09 g, 0.84 mmol) in 95% yield.
Workup
- temperaturewarmed to and
- stirringstirred at room temperature for 14 h
- washwashed with saturated NaHCO3 (10 mL×3)
- customdried over anhydrous K CO3
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by silica gel (deactivated by Et3N) column chromatography
Sources & evidence
- ORD record
- ord-a431ad9842ef448fb060c9cc79f49b18
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928266B2
Reaction notes
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