Benzoyl chloride → Propionate ion

HRID 373861Notes

Reaction equation

HRID 373861 reaction equation
[OH:1][C@H:2]1[C:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@@:5]3([OH:23])[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1.[C:24]([O:28]C(=O)CC)(=[O:27])[CH2:25][CH3:26].C(Cl)(=O)C1C=CC=CC=1>>[OH:23][C@:5]12[C@H:4]3[C@@H:13]([C@:14]4([CH3:21])[C:19]([C:2](=[O:1])[CH2:3]3)=[CH:18][C:17](=[O:20])[CH2:16][CH2:15]4)[CH2:12][CH2:11][C@:9]1([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]2.[C:24]([O-:28])(=[O:27])[CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 31263Propionic anhydrideHCID 9861812HCID 9861812, compound

Product 2

HCID 104745Propionate ionHCID 6918079120051-39-0

Procedure

The above compounds can be synthesized by the methods described in Japanese Patent Application Laid-Open Nos. 192794/1988 and 131193/1989. That is, 14α-hydroxy-4-androstene-3,6,17-trione is synthesized from 6β,14α-dihydroxy-4-androstene-3,17-dione according to an ordinary oxidation reaction (for example, Jones' oxidation reaction) and then is reacted with propionic anhydride or benzoyl chloride to obtain a propionate or a benzoate.

Workup

  1. customThe above compounds can be synthesized by the methods

Sources & evidence

ORD record
ord-63479b2df51e488eb4898015334d8643
Source dataset
uspto-grants-1992_11
Patent number
US05166200

Reaction notes

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