Potassium tert-butoxide → 6-cyano-2,2-dimethyl-4-(4-ethoxycarbonyl-1,2-dihydro-2-oxo-1-pyridinyl)-2H-benzo[b]pyran

HRID 487637Notes

Reaction equation

HRID 487637 reaction equation
CS(OC[C@@H:7]1[C:12]([CH3:14])([CH3:13])[O:11][C:10]2[CH:15]=[CH:16][C:17]([C:19]#[N:20])=[CH:18][C:9]=2[C@H:8]1[N:21]1[CH:26]=[CH:25][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23][C:22]1=[O:32])(=O)=O.CC(C)([O-])C.[K+]>O1CCCC1>[C:19]([C:17]1[CH:16]=[CH:15][C:10]2[O:11][C:12]([CH3:13])([CH3:14])[CH:7]=[C:8]([N:21]3[CH:26]=[CH:25][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23][C:22]3=[O:32])[C:9]=2[CH:18]=1)#[N:20]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86747680trans-3-methanesulfonyloxymethyl-6-cyano-3,4-dihydro-2,2-dimethyl-4-(4-ethoxycarbonyl-1,2-dihydro-2-oxo-1-pyridinyl)-2H-benzo[b]pyran

Product 1

HCID 190925696-cyano-2,2-dimethyl-4-(4-ethoxycarbonyl-1,2-dihydro-2-oxo-1-pyridinyl)-2H-benzo[b]pyranYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 8 ml of anhydrous tetrahydrofuran, is dissolved 250 mg of trans-3-methanesulfonyloxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(4-ethoxycarbonyl-1,2-dihydro-2-oxo-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 20. Then, 112 mg of potassium t-butoxide is added at room temperature, and the resulting mixture is reacted at that temperature for 40 minutes. The reaction mixture is concentrated under reduced pressure and the residue is dissolved in methylene chloride, washed with saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The inorganic matter is filtered off, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography using 1/2 mixture of ethyl acetate/n-hexane as a developing solvent. Thus, 109 mg of 6-cyano-2,2-dimethyl-4-(4-ethoxycarbonyl-1,2-dihydro-2-oxo-1-pyridinyl)-2H-benzo[b]pyran is obtained.

Workup

  1. customthe resulting mixture is reacted at that temperature for 40 minutes
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in methylene chloride
  4. washwashed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe inorganic matter is filtered off
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography
  9. addition1/2 mixture of ethyl acetate/n-hexane as a developing solvent

Sources & evidence

ORD record
ord-56bd1fb52fc94051a0ae5808429d098c
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

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