Chlorotrimethylsilane → HCID 15231285, compound

HRID 1415719Notes

Reaction equation

HRID 1415719 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[CH:14]([CH2:15][C:16](=[O:24])[CH:17]=[CH:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2].[CH2:25]1COC[CH2:26]1.C([Al](CC)CC)C.C[Si](Cl)(C)C>C1(C)C=CC=CC=1>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[CH:14]([CH2:15][C:16](=[O:24])[CH2:17][C@@H:18]1[CH2:25][CH3:26])[CH2:13][CH2:12]3)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 10969589HCID 10969589, compoundHCID 16682930Triethylaluminum

Product 1

HCID 15231285HCID 15231285, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.31 g (10 mmol) of 17β-acetoxy-androst-1-en-3-one and 143 mg (1 mmol) of CuBr are introduced into 15 ml of dry THF. 5.79 ml (11 mmol) of a 1.9 molar solution of triethylaluminum in toluene as well as 2.16 g (20 mmol) of trimethylsilyl chloride are added at 0° C. It is stirred for 1 hour at room temperature, then hydrolyzed with 10 ml of 2N hydrochloric acid and the product is extracted with methyl tert-butyl ether. After evaporation of the solvent and recrystallization from acetone, 3.2 g of 17β-acetoxy-1α-ethylandrostan-3-one (90% of theory) of melting point 159° C. is obtained.

Workup

  1. extractionhydrolyzed with 10 ml of 2N hydrochloric acid and the product is extracted with methyl tert-butyl ether
  2. customAfter evaporation of the solvent and recrystallization from acetone, 3.2 g of 17β-acetoxy-1α-ethylandrostan-3-one (90% of theory) of melting point 159° C.
  3. customis obtained

Sources & evidence

ORD record
ord-2a154aab85a149f582790795addf956d
Source dataset
uspto-grants-1999_06
Patent number
US05908945

Reaction notes

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