HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Isopropanol → 5-Ethoxycarbonyl-3-isopropoxycarbonyl-1,4-dihydro-2,6-dimethyl-4-(3-ethynylphenyl)pyridine

HRID 467127
Notes
Print preview

Reaction equation

HRID 467127 reaction equation
[C:1]([C:3]1[CH:4]=C([CH:8]=[CH:9][CH:10]=1)C=O)#[CH:2].[C:11]([O:17][CH:18]([CH3:20])[CH3:19])(=[O:16])[CH2:12][C:13]([CH3:15])=O.[NH2:21]/[C:22](/[CH3:29])=[CH:23]\[C:24]([O:26][CH2:27][CH3:28])=[O:25].[CH:30](O)(C)[CH3:31]>N1CCCCC1>[CH2:27]([O:26][C:24]([C:23]1[CH:13]([C:15]2[CH:8]=[CH:9][CH:10]=[C:3]([C:1]#[CH:2])[CH:4]=2)[C:12]([C:11]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])=[C:30]([CH3:31])[NH:21][C:22]=1[CH3:29])=[O:25])[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 68329Isopropyl acetoacetateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 27716443-Ethynylbenzaldehyde

Product 1

HCID 198134055-Ethoxycarbonyl-3-isopropoxycarbonyl-1,4-dihydro-2,6-dimethyl-4-(3-ethynylphenyl)pyridineYield 58.6%

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Procedure

To a mixture of 0.65 g (0.005 mol) of 3ethynylbenzaldehyde, 1.08 g (0.0075 mol) of isopropyl acetoacetate and 25 ml of isopropyl alcohol were added 2 to 3 drops of piperidine. After heating the mixture under reflux for 24 hours, 0.65 g (0.005 mol) of ethyl 3-aminocrotonate was added thereto, further the admixture was heated under reflux for 24 hours. After completing the reaction, the reaction mixture was concentrated. The obtained precipitate was purified by subjecting to silica gel column chromatography [eluent: n-hexane to n-hexane: ethyl acetate (7 : 3)] to give 1.1 g of the desired compound (yield: 58.6%).

Workup

  1. temperatureAfter heating the mixture
  2. temperatureunder reflux for 24 hours
  3. temperaturefurther the admixture was heated
  4. temperatureunder reflux for 24 hours
  5. customthe reaction
  6. concentrationthe reaction mixture was concentrated
  7. customThe obtained precipitate was purified

Sources & evidence

ORD record
ord-d00579241cd841498e28cdd9874272dc
Source dataset
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05158963

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes