Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Lithium | HCID 3028194 | — |
| Reactant | HCID 12876731 | HCID 12876731 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22820407 | HCID 22820407 | 95.4% |
Reaction Steps
A solution of 10.0 g of 3-methoxy-16α-methyl-1,3,5(10)-estratrien-17β-ol in 200 ml of absolute THF and 20 ml of tert.-butanol is dropped at -50° C. to about 500 ml of ammonia and then combined in incremental portions with 6.3 g of lithium. The mixture is agitated for 3 hours at -40° C., ammonia is allowed to evaporate overnight, the residue is taken up in about 1 liter of water, and extracted with ethyl acetate, thus obtaining 9.6 g of 3-methoxy-16α-methyl-2,5(10)-estradien-17β-ol as an amorphous crude product which is used in the subsequent stage without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04333928 |
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| Source dataset | uspto-grants-1982_06 |
|---|
| ORD ID | ord-9ea04bde159549209cb42293987e24d1 |
|---|
| Source note | uspto-grants-1982_06 |
|---|
