Reaction equation
[H-].[Na+].C[C:4]1([CH3:11])O[C@H:7]([CH2:9]O)[CH2:6][O:5]1.C(Br)C[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].O>C1COCC1>[CH2:6]([O:5][CH2:4][CH2:11][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])[CH2:7][CH2:9][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a stirred suspension of NaH (80%; 0.55 g, 17.4 mmol, 2 equiv) in THF (20 ml) was added dropwise a solution of (R)-glycerol acetonide 1 (1.15 g; 1 equiv) in THF (20 ml). After that octadecyl bromide (5.8 g, 17.4 mmol, 2 equiv) dissolved in THF (25 ml) was added dropwise and the mixture obtained was stirred overnight at 80° C. The reaction mixture was cooled to 0° C. and water was added. The resulting mixture was concentrated and the residue was extracted with water and diethyl ether and the combined extracts were dried (MgSO4). The crude product obtained was further purified by flash column chromatography (10% ethyl acetate-n-hexane) to yield the title compound 1b (2.03 g, 5.28 mmol, 61%).
Workup
- additionwas added dropwise
- customthe mixture obtained
- temperatureThe reaction mixture was cooled to 0° C.
- concentrationThe resulting mixture was concentrated
- extractionthe residue was extracted with water and diethyl ether
- dry with materialthe combined extracts were dried (MgSO4)
- customThe crude product obtained
- customwas further purified by flash column chromatography (10% ethyl acetate-n-hexane)
Sources & evidence
- ORD record
- ord-5c0e6097f7454a8ebf3a75ff760da7a9
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07465817B2
Linked notes
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