Hydrochloric Acid → 17beta-Ethoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

HRID 267610Notes

Reaction equation

HRID 267610 reaction equation
[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([OH:24])=[O:23])[CH2:3]1.Cl.[CH2:26](O)[CH3:27]>>[CH2:26]([O:23][C:22]([C@H:11]1[CH2:10][CH2:9][C@H:8]2[C@H:7]3[C@H:16]([C:15](=[O:21])[CH2:14][C@:12]12[CH3:13])[C@:17]1([CH3:20])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:19][CH2:18]1)[CH2:5][CH2:6]3)=[O:24])[CH3:27]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 227882653alpha-Hydroxy-5alpha-androstan-11-one 17beta-carboxylic acid

Product 1

HCID 8673312717beta-Ethoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

Procedure

A solution of 3α-hydroxy-11-oxo-5α-androstane-17β-carboxylic acid (500 mg.) in dry ethanol containing 3.3%, by weight, of hydrogen chloride (100 ml.) was refluxed for 2 hours.

Sources & evidence

ORD record
ord-d215b06033444778935584762096b918
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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