Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propargyl bromide | HCID 7842 | — |
| Reactant | Hydantoin | HCID 10006 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 15669662 | HCID 15669662 | 60.1% |
Reaction Steps
To a solution of hydantoin (10 g, 100 mmol) in THF (150 mL) add tetrabutylammonium bromide (4 g, 12.3 mmol), potassium hydroxide (5.6 g, 100 mmol) and then propargyl bromide (11.9 g, 100 mmol). Heat the mixture to 75° C. for 18 h. Dilute the mixture with EtOAc (200 mL), wash with water (2×100 mL) and 1N aqueous HCl (100 mL). Dry the organic phase over MgSO4, filter and concentrate in vacuo to obtain the title compound as a yellow powder (8.3 g, 60%). Triturate the solid with diethyl ether (100 mL) to obtain the title compound as a white crystalline solid (7.8 g, 56%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08420631B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-c76458333c7b4e76a0fe5ef96155123f |
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| Source note | uspto-grants-2013_04 |
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