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Acrylonitrile → 2-Cyanoethoxy-1,3-dimethoxyestra-1,3,5(10)-triene

HRID 839749
Notes
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Reaction equation

HRID 839749 reaction equation
[CH3:1][O:2][C:3]1[C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([OH:21])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]([O:22][CH3:23])[CH:4]=1.CC(C)([O-])C.[K+].[C:30](#[N:33])[CH:31]=[CH2:32]>C1C=CC=CC=1>[C:30]([CH2:31][CH2:32][O:21][CH2:14][C@:15]12[CH2:17][CH2:18][C@H:19]3[C@@H:10]([CH2:9][CH2:8][C:7]4[CH:6]=[C:5]([O:22][CH3:23])[CH:4]=[C:3]([O:2][CH3:1])[C:20]=43)[C@@H:11]1[CH2:12][CH2:13][CH2:16]2)#[N:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7855Acrylonitrile2×HCID 23665647Potassium tert-butoxide2×HCID 706144001,3-Dimethoxy-17beta-hydroxyestra-1,3,5(10)-triene

Product 1

HCID 867357812-Cyanoethoxy-1,3-dimethoxyestra-1,3,5(10)-triene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1,3-dimethoxy-17β-hydroxyestra-1,3,5(10)-triene (1.5 g, 4.7 mM), potassium t-butoxide (0.053 g, 0.47 mM) and acrylonitrile (0.5 g, 9.4 mM) in 25 ml of anhydrous benzene is refluxed with vigorous stirring for 5 hrs. An additional 0.5 g of acrylonitrile and 0.025 g of potassium t-butoxide are added; the solution is refluxed for 2 hrs and allowed to stir at room temperature for 18 hrs. The resulting suspension is filtered and the filtrate evaporated in vacuo to give an oily residue which is chromatographed on 100 g of neutral silica gel. Elution with chloroform gives an oil which after trituration with hexane gives 17β-(2-cyanoethoxy-1,3-dimethoxyestra-1,3,5(10)-triene, yield 1.06 g (60.6%); m.p. 142°-144° (toluene-hexane).

Workup

  1. temperaturethe solution is refluxed for 2 hrs
  2. stirringto stir at room temperature for 18 hrs
  3. filtrationThe resulting suspension is filtered
  4. customthe filtrate evaporated in vacuo
  5. customto give an oily residue which
  6. customis chromatographed on 100 g of neutral silica gel
  7. washElution with chloroform
  8. customgives an oil which after trituration with hexane

Sources & evidence

ORD record
ord-c0f53703165d4f16908fee1b70acdb4b
Source dataset
uspto-grants-1978_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04096253

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes