Ethanol → 2,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine

HRID 34415Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]([CH3:33])=[C:5]([C:21]([O:23][CH2:24][CH2:25][CH2:26]CCCCCBr)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[CH3:34][O:35][C:36](=O)[CH2:37][C:38]1[CH:43]=[CH:42][C:41](SCC2C=CC=CC=2)=[CH:40][CH:39]=1.[N+]([C:56]1[CH:57]=[C:58](C=CC=1)[CH:59]=[O:60])([O-])=O.C([OH:66])C>>[CH3:1][C:2]1[NH:3][C:4]([CH3:33])=[C:5]([C:21]([O:23][CH2:24][CH2:25][CH2:26][O:66][C:41]2[CH:40]=[CH:39][C:38]([CH2:37][CH2:36][O:35][CH:34]3[CH2:56][CH2:57][CH2:58][CH2:59][O:60]3)=[CH:43][CH:42]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

Reactant 4

HCID 702Ethanol

HCID 74493-Nitrobenzaldehyde

HCID 20129521HCID 20129521, compound

HCID 54174016Methyl(4-benzylthiophenyl)acetate

Product 1

HCID 142087862,6-Dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-[4-(2-tetrahydropyran-2-yloxyethyl)phenoxy]propoxycarbonyl)-1,4-dihydropyridine

Procedure

A mixture of 3-(4-[2-(tetrahydropyran-2-yloxy)ethyl]phenoxy)propyl acetoacetate (2, 5 g), methyl 3-aminocrotonate (3, 2.3 g), 3-nitrobenzaldehyde (4, 2.9 g) and ethanol (70 mL) is heated at reflux for about 12 hours. The solvent is removed under reduced pressure and the residue purified using silica gel chromatography (90/10CH2Cl2 /acetone) to yield 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-[3-(4-[2-(tetrahydropyran-2-yloxy)ethyl]phenoxy)propoxycarbonyl]-1,4-dihydropyridine (1, mp<55° C.).

Workup

temperatureis heated
temperatureat reflux for about 12 hours
customThe solvent is removed under reduced pressure
customthe residue purified

Sources & evidence

ORD record: ord-eb9ebf900137450299afcd3bf8520aa1
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04761420

Reaction notes

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