Acrylonitrile → 2-Cyanoethoxy-1,3-dimethoxyestra-1,3,5(10)-triene
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]Participants
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
- temperaturethe solution is refluxed for 2 hrs
- stirringto stir at room temperature for 18 hrs
- filtrationThe resulting suspension is filtered
- customthe filtrate evaporated in vacuo
- customto give an oily residue which
- customis chromatographed on 100 g of neutral silica gel
- washElution with chloroform
- customgives an oil which after trituration with hexane
Sources & evidence
- ORD record
- ord-c0f53703165d4f16908fee1b70acdb4b
- Source dataset
- uspto-grants-1978_06
- Patent number
- US04096253
Reaction notes
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