Sodium hydride → 2,2-Dimethyl-4-(2-oxopiperidin-1-yl)-2H-1-benzopyran-6-carbonitrile

HRID 1905783Notes

Reaction equation

HRID 1905783 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][C:12]([CH3:15])([CH3:14])[C@@H:11](O)[C@H:10]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C:18]3=[O:23])[C:9]=2[CH:24]=1)#[N:4]>O1CCCC1>[C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][C:12]([CH3:15])([CH3:14])[CH:11]=[C:10]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C:18]3=[O:23])[C:9]=2[CH:24]=1)#[N:4]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 131511766-cyano-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-2H-benzo[b]pyran-3-ol

Product 1

HCID 137043562,2-Dimethyl-4-(2-oxopiperidin-1-yl)-2H-1-benzopyran-6-carbonitrileYield 4.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (170 mg, 80% dispersion in oil) was added to a solution of trans-6-cyano-3,4-dihydro-2,2-dimethyl-4-(2-oxo-1-piperidinyl)-2H-1-benzopyran-3-ol (1.65 g) in anhydrous tetrahydrofuran (25 ml) and the reaction mixture stirred and heated under reflux for 48 hours. Work up as in Example 1, followed by chromatography (chromatotron--2 mm Silica gel HF254 --elution with ethyl acetate at 6 ml/min) gave one fraction (312 mg) which on recrystallisation from ethyl acetate gave the title compound as crystals (66 mg) of m.p. 162°-163° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 48 hours
  3. washWork up as in Example 1, followed by chromatography (chromatotron--2 mm Silica gel HF254 --elution with ethyl acetate at 6 ml/min)
  4. customgave one fraction (312 mg) which
  5. customon recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-4024f5d8b99e435f97d39747f9dd7075
Source dataset
uspto-grants-1987_03
Patent number
US04647670

Reaction notes

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