Diethyl Ether → HCID 86735676, compound

HRID 371808Notes

Reaction equation

HRID 371808 reaction equation
[CH3:1][C@:2]12[CH2:20][CH2:19][C@H:18]3[C@@H:7]([CH:8]=[CH:9][C:10]4[C@:15]3([CH:16]=[O:17])[CH2:14][CH2:13][C:12](=[O:21])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][CH2:3]2.[CH2:22](OCC)C.CCCCCC>O1CCCC1>[CH3:22][C@@H:8]1[CH:9]=[C:10]2[C@:15]([CH:16]=[O:17])([CH2:14][CH2:13][C:12](=[O:21])[CH2:11]2)[C@@H:18]2[C@@H:7]1[C@H:6]1[C@@:2]([CH2:20][CH2:19]2)([CH3:1])[CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8058HexaneHCID 53709094HCID 53709094, compound

Product 1

HCID 86735676HCID 86735676, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The 7α-methyl-4-androstene-3,19-diones are produced by alkylating the corresponding 4,6-androstadiene-3,19-dione with dimethyllithium copper in an inert solvent such as diethyl ether, tetrahydrofuran, hexane or mixtures of these at temperatures ranging from -78° C. to 25° C. Tetrahydrofuran is the preferred solvent and temperatures between -5° C. to 10° C. provide optimum results. Quenching the initially formed enolate anion with a weak protonating agent such as a saturated solution of ammonium chloride, oxalic acid or boric acid provides the 7α-methyl-5-androstene-3,19-dione. Quenching the enolate with a strong protonating agent such as hydrochloric acid provides the 7α-methyl-4-androstene-3,19-diones.

Workup

  1. customranging from -78° C. to 25° C
  2. custombetween -5° C. to 10° C.
  3. customprovide optimum results
  4. customQuenching the initially formed enolate anion with a weak protonating agent such as a saturated solution of ammonium chloride, oxalic acid or boric acid

Sources & evidence

ORD record
ord-af6a81cc412b4119ac46fd0c13e25ee2
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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