Benzaldehyde → HCID 21539628, compound

HRID 1076269Notes

Reaction equation

[CH3:1][C:2]([CH3:10])([CH3:9])[C:3](=[O:8])[CH2:4][C:5](=[O:7])[CH3:6].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-:19].[NH4+:20].Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>>[C:2]([C:3]([C:4]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4]([C:3]([C:2]([CH3:10])([CH3:9])[CH3:1])=[O:19])=[C:5]([CH3:6])[N:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:5]=1[CH3:6])=[O:8])([CH3:10])([CH3:9])[CH3:1].[C:5]([C:4]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4]([C:5](=[O:7])[CH3:6])=[C:3]([C:2]([CH3:10])([CH3:9])[CH3:1])[N:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:3]=1[C:2]([CH3:10])([CH3:9])[CH3:1])(=[O:19])[CH3:6]

Participants

Reactant 4

HCID 240Benzaldehyde

HCID 10928Ethyl chloroformate

HCID 14923Ammonium Hydroxide

HCID 817415,5-Dimethylhexane-2,4-dione

Product 2

HCID 21539628HCID 21539628, compound

HCID 21539664HCID 21539664, compound

Procedure

Similarly, reaction of 5,5-dimethyl-2,4-hexanedione, benzaldehyde and ammonium hydroxide by the procedure of Example 6 with separation of the 1,4-dihydropyridines thus obtained and subsequent treatment with ethyl chloroformate as described above gives 3,5-di-t-butylcarbonyl-1-carbethoxy-1,4-dihydro-2,6-dimethyl-4-phenylpyridine and 3,5-diacetyl-2,6-di-t-butyl-1-carbethoxy-1,4-dihydro-4-phenylpyridine.

Workup

customwith separation of the 1,4-dihydropyridines
customthus obtained

Sources & evidence

ORD record: ord-6220eca2044b408cbd59791f6f06fae5
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03956341

Reaction notes

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