Sodium Hydroxide → HCID 22941790, compound

HRID 1603331Notes

Reaction equation

HRID 1603331 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH:18]=[CH:17][C:16]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[CH:15][C:14]=1[CH2:13][C@H:12]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35]C(=O)C)(=[O:3])[CH3:2].[OH-].[Na+]>CO.C(OCC)C>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH:18]=[CH:17][C:16]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[CH:15][C:14]=1[CH2:13][C@H:12]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22941789HCID 22941789, compound

Product 1

HCID 22941790HCID 22941790, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 10.2 g of 17β-acetoxy-7α-(5-acetoxypentyl)-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene in 205 ml of methanol is stirred with 33.7 ml of sodium hydroxide solution for 45 minutes at 15° C. Then, it is diluted with diethyl ether, washed with water, dried on sodium sulfate and concentrated by evaporation in a vacuum. 5.6 g of 17β-acetoxy-7α-(5-hydroxypentyl)-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene is obtained. [α]D22 =+32.2° (c=0.505% in chloroform)

Workup

  1. washwashed with water
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-8afe3d0684d548ebbc21ac1934a9ac4b
Source dataset
uspto-grants-1999_11
Patent number
US05986115

Reaction notes

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