Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Glycidyl tosylate, (R)- | HCID 154187 | — |
| Catalyst | HCID 178478939 | HCID 178478939 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 15476078 | HCID 15476078 | 190.2% |
Reaction Steps
In a 500 ml flask was put 18 ml of a 0.1 ML-1 solution of lithium copper tetrachloride in dried THF, followed by cooling to -50° C. The above prepared Grignard reagent was added thereto over 5 minutes, and the mixture was reacted at that temperature for 20 minutes. To the reaction mixture was added dropwise a solution of 8.07 g of (R)-glycidyl p-toluenesulfonate (produced by Aldrich Chemical Co., Inc.) in 70 ml of dried THF at the same temperature over 20 minutes through a dropping funnel, followed by further reacting for 1.5 hours. The resulting reaction mixture was poured into a saturated ammonium chloride aqueous solution and extracted with diethyl ether. The extract was washed twice with a saturated sodium chloride aqueous solution, and the solvent was removed by distillation under reduced pressure to obtain 10.1 g (95%) of a crude product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06093345 |
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| Source dataset | uspto-grants-2000_07 |
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| ORD ID | ord-c10098b343d0402f9838b38aa281f156 |
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| Source note | uspto-grants-2000_07 |
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