Chloroacetonitrile → 2-[(3,4-Dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetonitrile

HRID 867991Notes

Reaction equation

[Cl:1][C:2]1[C:3]([OH:21])=[CH:4][C:5]2[CH2:6][CH2:7][C:8]3([CH2:18][CH2:19][CH3:20])[C:13]([C:14]=2[C:15]=1[Cl:16])=[CH:12][C:11](=[O:17])[CH2:10][CH2:9]3.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:29][C:30]#[N:31]>CN(C)C=O>[Cl:1][C:2]1[C:3]([O:21][CH2:29][C:30]#[N:31])=[CH:4][C:5]2[CH2:6][CH2:7][C:8]3([CH2:18][CH2:19][CH3:20])[C:13]([C:14]=2[C:15]=1[Cl:16])=[CH:12][C:11](=[O:17])[CH2:10][CH2:9]3

Participants

Conditions

Temperature: 65 °C

Procedure

A stirred mixture of 3,4-dichloro-6,7,8,8a,9,10-hexahydro-2-hydroxy-6-oxo-8a-propylphenanthrene (0.4 g, 1.22 mmole), potassium carbonate (0.2 g, 1.45 mmole) and chloroacetonitrile (160 μl, 1.78 mmole) in dimethylformamide (7 ml) is heated at 65° C. for 2 hours, poured into ice water, extracted with ether, washed with water, brine, dried over MgSO4 and evaporated in vacuo. Trituration of the residual oil with butyl chloride give 2-[(3,4-dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetonitrile which is removed by filtration, and dried.

Workup

extractionextracted with ether
washwashed with water, brine
dry with materialdried over MgSO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-15ae3c2fb8f941b686a7c04f9561958e
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04777281

Reaction notes

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