Ethyl formate → 5-Ethynyl-5-(4-methoxy-dibenzofuran-1-yl)-2-oxo-cyclohexanecarbaldehyde

HRID 2383979Notes

Reaction equation

HRID 2383979 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16]2([C:23]#N)[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)=[CH:5][CH:4]=1.C1C[O:28][CH2:27]C1.[CH:30](OCC)=O>>[C:23]([C:16]1([C:6]2[C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[O:9][C:8]=3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:21][CH:20]([CH:27]=[O:28])[C:19](=[O:22])[CH2:18][CH2:17]1)#[CH:30]

Participants

4

Reactant 3

HCID 8025Ethyl formateHCID 8028TetrahydrofuranHCID 248041271-(4-Methoxy-dibenzofuran-1-yl)-4-oxo-cyclohexane carbonitrile

Product 1

HCID 866358295-Ethynyl-5-(4-methoxy-dibenzofuran-1-yl)-2-oxo-cyclohexanecarbaldehyde

Procedure

At 0° C., to a solution of the cyclic ketone 1-(4-methoxy-dibenzofuran-1-yl)-4-oxo-cyclohexane carbonitrile (0.5 g, 0.00156 mol) (as obtained in example 2) in THF (15 ml) sodium methoxide (0.093 g, 0.0017 mol) was added and the reaction mass was stirred for 15 min. Then ethyl formate (0.15 ml, 0.0018 mol) was added at 0° C., and the reaction mass was refluxed for 1 hr. Once product has 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. The product 5-ethynyl-5-(4-methoxy-dibenzofuran-1-yl)-2-oxo-cyclohexanecarbaldehyde was isolated by column chromatography. Yield 0.250 g (46%)

Workup

  1. temperaturethe reaction mass was refluxed for 1 hr
  2. customOnce product has formed
  3. customthe reaction mass was quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0e511fa79fa44697b35878c132b054d7
Source dataset
uspto-grants-2012_09
Patent number
US08263648B2

Reaction notes

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