Sodium hydride → HCID 13563078, compound
Reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][CH:11]([CH2:14][OH:15])[O:12][CH3:13].[O:16]1[CH:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:17]1>CCCCCC>[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][CH:11]([O:12][CH3:13])[CH2:14][O:15][CH2:17][CH:18]([OH:16])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Sodium hydride (50% in oil) (1.74 g, 36.3 mmoles) was washed with n-hexane and dried in a nitrogen gas stream. After addition of 80 ml of dry DMSO, the mixture was heated on a water bath at 70° C. for 30 minutes. When the mixture became homogeneous, 6.9 g (36.3 mmoles) of 2-methylglycerol tetrahydropyranyl ether was added dropwise and, after 15 minutes, 4.62 g (18.2 mmoles) of 1,2-epoxyheptadecane was added dropwise. The mixture was stirred at 70° C. for an hour, poured into 100 ml of broken ice and extracted with 300 ml of n-hexane-ethyl acetate (1:1). The extract was washed with water, dried and concentrated and the residue was purified by silica gel column chromatography to give 4.37 g (53.9%) of the desired compound as a colorless oil.
Workup
- customdried in a nitrogen gas stream
- additionAfter addition of 80 ml of dry DMSO
- extractionextracted with 300 ml of n-hexane-ethyl acetate (1:1)
- washThe extract was washed with water
- customdried
- concentrationconcentrated
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-ff4d22b637044f04a94edf04fee7771e
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04649203
Reaction notes
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