Reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[O:6][CH:7]([CH2:10][OH:11])[CH2:8][OH:9].[C:12](O[K])([CH3:15])([CH3:14])C.C1(C)C=CC(S(O[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH2:45]([O:11][CH2:10][CH:7]([CH2:8][O:9][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]/[CH:34]=[CH:33]\[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:14][CH2:12][CH3:15])[O:6][CH:2]1[CH2:3][CH2:4][CH2:5][O:1]1)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]/[CH:37]=[CH:36]\[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH3:28]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In 30 ml of xylene was dissolved 854 mg (5.3 mmol) of 2-O-tetrahydrofuranylglycerol. To this was added 1.78 g (15.9 mmol) of t-butoxypotassium under argon gas and the mixture was stirred for 5 minutes. Then, 10 ml of a solution of 6.71 g (15.9 mmol) oleyl p-toluenesulfonate in xylene was added dropwise and the mixture was stirred under reduced pressure (20-30 mmHg) at ambient temperature for 30 minutes and further at 50° C. for 1 hour. This reaction mixture was poured in ice-water and extracted with ether, and the extract was washed with water, dried, and concentrated. The residue was purified by column chromatography (silica gel/chloroform) to provide 628 mg (18%) of 1,3-O-dioleyl-2-O-tetrahydrofuranylglycerol as yellow oil.
Workup
- stirringthe mixture was stirred under reduced pressure (20-30 mmHg) at ambient temperature for 30 minutes and further at 50° C. for 1 hour
- extractionextracted with ether
- washthe extract was washed with water
- customdried
- concentrationconcentrated
- customThe residue was purified by column chromatography (silica gel/chloroform)
Sources & evidence
- ORD record
- ord-9357d88419b74d578cfe1241262cd1df
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05705188
Linked notes
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