(E,E)-5-(3beta,14beta-dihydroxy-5beta-androstane-17beta-yl)-2,4-pentadien-1-ol → (E,E)-5-(3beta,14beta-Dihydroxy-5beta-androstane-17beta-yl)-2,4-penta-dienal

HRID 1080634Notes

Reaction equation

HRID 1080634 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[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@:8]3([OH:27])[CH2:9][CH2:10][C@@H:11]2/[CH:21]=[CH:22]/[CH:23]=[CH:24]/[CH2:25][OH:26])[CH2:3]1>C(Cl)(Cl)Cl.C(O)(C)C.O=[Mn]=O>[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[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@:8]3([OH:27])[CH2:9][CH2:10][C@@H:11]2/[CH:21]=[CH:22]/[CH:23]=[CH:24]/[CH:25]=[O:26])[CH2:3]1

Participants

5

Reactant 1

HCID 10738195(E,E)-5-(3beta,14beta-dihydroxy-5beta-androstane-17beta-yl)-2,4-pentadien-1-ol

Product 1

HCID 10523343(E,E)-5-(3beta,14beta-Dihydroxy-5beta-androstane-17beta-yl)-2,4-penta-dienalYield 98.5%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 4.90 g of (E,E)-5-(3β,14β-dihydroxy-5β-androstane-17β-yl)-2,4-pentadien-1-ol in 160 ml of chloroform and 40 ml of iso-propanol, 10.40 g of MnO2 were added at room temperature. The mixture was stirred overnight and then filtered through Celite. The organic solution was evaporated to dryness to give 4.80 g of the title compound (II-a) as an off-white solid.

Workup

  1. filtrationfiltered through Celite
  2. customThe organic solution was evaporated to dryness

Sources & evidence

ORD record
ord-fed7006946344ed4847395e87574281f
Source dataset
uspto-grants-1996_12
Patent number
US05583127

Reaction notes

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