Lithium → HCID 131710545, compound

HRID 1731019Notes

Reaction equation

HRID 1731019 reaction equation
[C:1]([O:4][C@@:5]1([C:26]#[CH:27])[C@@H:11]2[CH2:12][C@@H:10]2[C@H:9]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:6]12[CH2:7][CH3:8])[C@@H:21]1[C:16](=[CH:17][C:18](=[O:25])[CH2:19][CH2:20]1)[CH2:15][CH2:14]3)(=[O:3])[CH3:2].[Li]>O1CCCC1>[OH:25][C@H:18]1[CH2:19][CH2:20][C@H:21]2[C:16]([CH2:15][CH2:14][C@@H:13]3[C@@H:22]2[CH2:23][CH2:24][C@@:6]2([CH2:7][CH3:8])[C@H:9]3[C@H:10]3[CH2:12][C@H:11]3[C@@:5]2([O:4][C:1](=[O:3])[CH3:2])[C:26]#[CH:27])=[CH:17]1

Participants

4

Reactant 2

HCID 3028194LithiumHCID 131710546HCID 131710546, compound

Product 1

HCID 131710545HCID 131710545, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg. of natural 17β-acetoxy-18-methyl-17α-ethinyl-15α,16α-methylene-4-estren-3-one is mixed in 20 ml. of absolute tetrahydrofuran with 670 mg. of lithium tri-tert.-butoxyalanate and agitated for 1 hour at room temperature. The mixture is then worked up analogously to Example 17. After chromatography on silica gel, 160 mg. of natural 3β-hydroxy-17β-acetoxy-18-methyl-17α-ethinyl-15α,16α-methylene-4-estrene is obtained.

Sources & evidence

ORD record
ord-c179a6f5bed54a3fad61df403d7543bd
Source dataset
uspto-grants-1976_11
Patent number
US03994937

Reaction notes

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