Ethyl trichloroacetate → HCID 86746643, compound

HRID 1613979Notes

Reaction equation

HRID 1613979 reaction equation
[CH2:1]1[CH2:26][O:25][C:3]2([CH2:20][CH2:19][C@@:18]3([CH3:21])[C:5](=[CH:6][CH2:7][C@@H:8]4[C@:17]3([OH:22])[CH2:16][CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][C@H:11]([CH3:24])[C:12]3=O)[CH2:4]2)[O:2]1.[Cl:27][C:28](Cl)(Cl)[C:29]([O:31][CH2:32][CH3:33])=[O:30].[Cl-].C([Al+]CC)C>[Zn].C1(C)C=CC=CC=1.CC(C)=O>[Cl:27]/[C:28](=[C:12]1\[C@@H:11]([CH3:24])[CH2:10][C@@H:9]2[C@:13]\1([CH3:14])[CH2:15][CH2:16][C@@:17]1([OH:22])[C@H:8]2[CH2:7][CH:6]=[C:5]2[C@:18]1([CH3:21])[CH2:19][CH2:20][C:3]1([O:25][CH2:26][CH2:1][O:2]1)[CH2:4]2)/[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

6

Reactant 3

HCID 10588Ethyl trichloroacetateHCID 15126712HCID 15126712, compoundHCID 16686102Diethyl aluminum chloride

Product 1

HCID 86746643HCID 86746643, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 20247278Toluene acetoneSolvent

Procedure

Using the procedure of Example 18, 3,3-ethylenedioxy-9α-hydroxy-16β-methylandrost-5-en-17-one (3.60 g) was reacted with ethyl trichloroacetate (2.78 ml) in the presence of zinc dust (2.83 g) and diethylaluminium chloride (20 ml, 1M in hexane). Chromatography (silica gel, toluene/acetone 3/1) of the crude product (3.0 g) afforded the title compound as a single isomer.

Sources & evidence

ORD record
ord-8250c1b8d5ec48cda16fe962fb0cfa07
Source dataset
uspto-grants-1993_03
Patent number
US05194602

Reaction notes

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