Imidazole → Trimethyl[(oct-1-yn-4-yl)oxy]silane
Reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5].N1C=CN=C1.Cl[Si:16]([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O>[CH3:17][Si:16]([CH3:19])([CH3:18])[O:1][CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a cold solution of 166 g of 4-hydroxy-1-octyne [Prostaglandins, 10, 289 (1975)], and 240 g of imidazole in one liter of dimethylformamide is added dropwise 202 g of chlorotrimethylsilane. The mixture is allowed to stand at room temperature for 2 to 3 days. The mixture is partitioned with water and hexane. The hexane layer is washed with brine, dried over magnesium sulfate, and concentrated. Distillation of the residue gives a colorless liquid, b.p. 38° (0.2 mm).
Workup
- customThe mixture is partitioned with water and hexane
- washThe hexane layer is washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- distillationDistillation of the residue
- customgives a colorless liquid, b.p. 38° (0.2 mm)
Sources & evidence
- ORD record
- ord-2f4fa7703f1340d18e8a21b0d3ae9144
- Source dataset
- uspto-grants-1981_07
- Patent number
- US04281153
Reaction notes
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