HCID 19760396, compound → HCID 19760395, compound

HRID 1587013Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[C:16]([CH2:17][OH:18])=[C:15]([CH3:19])[N:14]([CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13]([CH3:29])=[C:12]2[C:30]#[N:31])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>ClC(Cl)C.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[C:16]([CH:17]=[O:18])=[C:15]([CH3:19])[N:14]([CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13]([CH3:29])=[C:12]2[C:30]#[N:31])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 13 mg (0.026 mmol) of 1,4-dihydro-4-(3,4-dimethoxyphenyl)-2,6-dimethyl-1-(3-phenylpropyl) -3-cyano-5-hydroxymethylpyridine in 0.45 ml of dichloroethane was added 5 mg of activated manganese dioxide. The mixture was heated at 80° C. for one hour. Then the mixture was filtered and concentrated. The resulting residue was purified by thin layer chromatography (AcOEt:Hexane 1:1) to give 7.4 mg (0.015 mmol) of 1,4-dihydro-4-(3,4-dimethoxyphenyl)-2,6-dimethyl -1-(3-phenylpropyl)-3-cyano-5-formylpyridine (yield: 58%).

Workup

filtrationThen the mixture was filtered
concentrationconcentrated
customThe resulting residue was purified by thin layer chromatography (AcOEt:Hexane 1:1)

Sources & evidence

ORD record: ord-e9b66de7ca60484c9135fbfd6ec4d051
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05216172

Reaction notes

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