Sodium Chloride → 1-(4-Methoxy-dibenzofuran-1-yl)-4-oxo-cyclohexane carbonitrile

HRID 2383976

Reaction equation

COC([CH:5]1[CH2:10][C:9]([C:26]#[N:27])([C:11]2[C:19]3[C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[O:16][C:15]=3[C:14]([O:24][CH3:25])=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6]1=[O:28])=O.[Cl-].[Na+]>CS(C)=O.O>[CH3:25][O:24][C:14]1[C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[C:19]=2[C:11]([C:9]2([C:26]#[N:27])[CH2:8][CH2:7][C:6](=[O:28])[CH2:5][CH2:10]2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 135 °C

Procedure

To a solution of 5-cyano-5-(4-methoxy-dibenzofuran-1-yl)-2-oxo-cyclohexane carboxylic acid methyl ester obtained in example 1 (7 g, 0.0185 mol) in DMSO (140 ml) and water (9 ml) was added sodium chloride (7 g, 0.119 mol) at room temperature. The reaction mass was heated to 130-140° C. for 5 hrs. Once the product is formed, the reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was dried with sodium sulfate and concentrated under vacuum. 1-(4-methoxy-dibenzofuran-1-yl)-4-oxo-cyclohexane carbonitrile was isolated by column chromatography. Yield 4.2 g (71%)

Workup

customOnce the product is formed
customthe reaction mass was quenched with water
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried with sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-c7d7fbdaa2f94d4e93cbd2f991291e96
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263648B2

Linked notes

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