Reaction equation
[H-].[Na+].[Na+].[I-].C[C:6]1([CH3:13])[O:10][CH:9]([CH2:11][OH:12])[CH2:8][O:7]1.S(C1C=CC(C)=CC=1)(O[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]CC)(=O)=O>CN(C=O)C.O>[CH2:6]([O:7][CH2:8][CH:9]([CH2:11][OH:12])[OH:10])[CH2:13][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of NaH (4.8 g, 120 mmol) and NaI (0.2 g) in dry DMF (20 mL) was added solketal (5.0 mL, 40 mmol) dropwise over a 30 min period. Once the effervescence had stopped, oleyl tosylate (Compound 13) (16.9 g, 40 mmol) was added and the reaction mixture was left for 3 days at 50° C. Then, H2O (10 mL) was added and the mixture was extracted with diethyl ether (2×100 mL), the combined organic phases were dried (MgSO4) and evaporated to dryness. The residue was taken up in THF (150 mL), 2M HCl was added until the solution turned turbid and the reaction was left to stir for 16 hours. The mixture was concentrated and subjected to silica-gel column chromatography [eluent: ethyl acetate/hexane, 50/50, v/v] to give 1-O-oleyl-rac-glycerol (Compound 20) as an oil.
Workup
- extractionthe mixture was extracted with diethyl ether (2×100 mL)
- dry with materialthe combined organic phases were dried (MgSO4)
- customevaporated to dryness
- addition2M HCl was added until the solution
- waitthe reaction was left
- concentrationThe mixture was concentrated
Sources & evidence
- ORD record
- ord-d585c376d5b54cdf94295f6c69d773c9
- Source dataset
- uspto-grants-2005_09
- Patent number
- US06949529B2
Linked notes
Loading…