Dimethyl Sulfoxide → Ethyl [(5-oxopentyl)oxy]acetate
Reaction equation
CS(C)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(N(CC)CC)C>C(Cl)Cl>[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:18]Participants
Conditions
- Temperature
- -60 °C
Procedure
To a solution of dimethylsulphoxide (18.6 ml, 263 mmol) in 75 ml of CH2Cl2 at -60° C. under nitrogen, is added dropwise a solution of trifluoroacetic anhydride (27.8 ml, 197 mmol) in 75 ml of CH2Cl2, over about 15 minutes. The reaction mixture is stirred for a further 15 minutes at -60° C. and the hydroxy/ester (1) (25 g, 132 mmol) in 150 ml CH2Cl2 is then added at such a rate as to keep the reaction temperature below -60° C. (over about 30 minutes). After a further 15 minutes at this temperature, triethylamine (55 ml, 395 mmol) is added slowly over about 15 minutes, the reaction mixture is allowed to warm to ambient temperature (about 1.5 hours) and is then quenched with water. The product is isolated by extraction with dichloromethane and purified by chromatography on Florisil to provide the title compound as an oil (20.7 g, 84%), νmax (film) 1750, 1725, 1195, 1130 cm-1.
Workup
- customthe reaction temperature below -60° C. (over about 30 minutes)
- temperatureto warm to ambient temperature (about 1.5 hours)
- customis then quenched with water
- customThe product is isolated by extraction with dichloromethane
- custompurified by chromatography on Florisil
Sources & evidence
- ORD record
- ord-7184ede34e404a8893fd7629ac1af93c
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05077309
Reaction notes
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