Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | HCID 15307268 | HCID 15307268 | — |
| Reactant | (Difluoromethyl)(oxo)diphenyl-lambda~5~-phosphane | HCID 15635908 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 18397082 | HCID 18397082 | 100.4% |
Reaction Steps
A solution of 715 mg of difluoromethyldiphenylphosphine oxide in 36 ml of tetrahydrofuran is slowly mixed with 1.42 ml of 2 M lithium diisopropylamide solution at a bath temperature of -50° C., and it is stirred for 1 hour. Then, a solution of 1 g of 3-tetrahydropyranyloxy-estra-1,3,5(10),6-tetraen-17-one in 10 ml of tetrahydrofuran is slowly added, stirred for 15 minutes, slowly heated at a bath temperature of from -50° C. to 100° C. and refluxed for 2.5 hours. For working-up, it is added to water, extracted with ethyl acetate, washed with water as well as with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. 1.1 g of 17-difluoromethylene-3-tetrahydropyranyloxy-estra-1,3,5(10), 6-tetraene is obtained as colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06136800 |
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| Source dataset | uspto-grants-2000_10 |
|---|
| ORD ID | ord-326896507def4beea4fac8626f6d05c4 |
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| Source note | uspto-grants-2000_10 |
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