Reaction equation
[Cl:1][CH2:2][CH2:3][O:4][CH2:5][C:6]([OH:8])=[O:7].OS(O)(=O)=O.[CH2:14](O)[CH3:15]>>[CH2:14]([O:7][C:6](=[O:8])[CH2:5][O:4][CH2:3][CH2:2][Cl:1])[CH3:15]Participants
4
Procedure
54.1 g (390 mmol) M24 obtained from the preceding reaction step was dissolved in 380 ml absolute ethanol and 9 ml conc. H2SO4 was added. The mixture was heated at reflux for 18 hours. Most of the ethanol was evaporated and the residue was dissolved in 400 ml CHCl3/100 ml water and basified with powder NaHCO3. The organic phase was washed with 2×400 ml saturated NaHCO3 and dried over Na2SO4. The solvent was evaporated to afford 58.3 g clear oil (yield: 89%).
Workup
- temperatureThe mixture was heated
- temperatureat reflux for 18 hours
- customMost of the ethanol was evaporated
- dissolutionthe residue was dissolved in 400 ml CHCl3/100 ml water and basified with powder NaHCO3
- washThe organic phase was washed with 2×400 ml saturated NaHCO3
- dry with materialdried over Na2SO4
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-05a4b7d3991b4ddcb9ef706af3926760
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06171866B2
Linked notes
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