Benzyl Bromide → 3-Benzyloxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetra-en-17-one

HRID 361664Notes

Reaction equation

HRID 361664 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH:10]=[CH:9]4)[C@H:6]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[CH2:5][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CC(C)=O>[CH2:33]([O:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH:10]=[CH:9]4)[C@H:6]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[CH2:5][C:4]=2[CH:3]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 158381633-Hydroxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-17-one

Product 1

HCID 572721663-Benzyloxy-7alpha-(5-hydroxypentyl)-estra-1,3,5(10),15-tetra-en-17-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2.85 g of 3-hydroxy-7α-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-17-one in 57 ml of acetone is mixed with 3.25 g of cesium carbonate and 1.14 ml of benzyl bromide, and the mixture is refluxed for 1 hour. The reaction mixture is concentrated by evaporation, the residue is mixed with water, shaken out with ethyl acetate, the organic phase is dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with hexane/ethyl acetate. 3.12 g of 3-benzyloxy-7α-(5-hydroxypentyl)-estra-1,3,5(10),15-tetraen-17-one is obtained as foam.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. additionthe residue is mixed with water
  4. customthe organic phase is dried on sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-e50b2b66eee14950bbc54d54b4b7f168
Source dataset
uspto-grants-1999_02
Patent number
US05866560

Reaction notes

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