Lithium Hydroxide → 3-Benzyloxy-17,17-ethylenedioxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraene

HRID 1603333Notes

Reaction equation

HRID 1603333 reaction equation
[CH2:1]1[CH2:29][O:28][C:3]2([CH:8]=[CH:7][C@H:6]3[C@H:9]4[C@H:18]([CH2:19][CH2:20][C@:4]23[CH3:5])[C:17]2[CH:16]=[CH:15][C:14]([OH:21])=[CH:13][C:12]=2[CH2:11][C@H:10]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[O:2]1.[OH-].[Li+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:32]([O:21][C:14]1[CH:15]=[CH:16][C:17]2[C@@H:18]3[C@H:9]([C@H:6]4[C@@:4]([CH2:20][CH2:19]3)([CH3:5])[C:3]3([O:2][CH2:1][CH2:29][O:28]3)[CH:8]=[CH:7]4)[C@H:10]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[CH2:11][C:12]=2[CH:13]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 7498Benzyl BromideHCID 5702379917,17-Ethylenedioxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-3-ol

Product 1

HCID 571990303-Benzyloxy-17,17-ethylenedioxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 32.7 g of 17,17-ethylenedioxy-7α-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-3-ol (see Example 1h) in 327 ml of dimethylformamide is mixed at room temperature with 5.73 g of lithium hydroxide and stirred with 15.1 ml of benzyl bromide for 2 hours at 60° C. Then, it is diluted with ethyl acetate, washed with water, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with dichloromethanenimethanol. 32.8 g of 3-benzyloxy-17,17-ethylenedioxy-7α-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraene is obtained.

Workup

  1. washwashed with water
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with dichloromethanenimethanol

Sources & evidence

ORD record
ord-39b724be347b4c8184c9badc9b91eec4
Source dataset
uspto-grants-1999_11
Patent number
US05986115

Reaction notes

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