HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → Rac. 8-(5-hydroxy-3-methyl-pent-3-en-1-yn-1-yl)-7,9,9-trimethyl-1,4-dioxaspiro[4,5]dec-6-en-8-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Lithium | HCID 3028194 | — |
| Reactant | 7,9,9-Trimethyl-1,4-dioxaspiro[4.5]dec-6-en-8-one | HCID 11769425 | — |
| Catalyst | Ferric nitrate | HCID 25251 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | Rac. 8-(5-hydroxy-3-methyl-pent-3-en-1-yn-1-yl)-7,9,9-trimethyl-1,4-dioxaspiro[4,5]dec-6-en-8-ol | HCID 131711512 | — |
Reaction Steps
Keto-α-isophorone is acetalized. The resulting 7,9,9-trimethyl-1,4-dioxaspiro[4,5]dec-6-en-8-one is condensed with trans-1-hydroxy-3-methyl-pent-2-en-4-yne in the presence of lithium in liquid ammonia and iron-(III) nitrate in ether to give rac. 8-(5-hydroxy-3-methyl-pent-3-en-1-yn-1-yl)-7,9,9-trimethyl-1,4-dioxaspiro[4,5]dec-6-en-8-ol (XVI).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04156090 |
| Source dataset | uspto-grants-1979_05 |
| ORD ID | ord-f1785cc8c6c04947a40028dfef09b865 |
| Source note | uspto-grants-1979_05 |