Dimethyl acetylenedicarboxylate → 1-(3-Methoxy-4-ethoxyphenyl)-2,3-bis(methoxycarbonyl)-4-hydroxy-6,7,8-trimethoxynaphthalene

HRID 622464

Reaction equation

CO[CH:3]([O:17]C)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[C:5]=1Br.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH3:31])[CH:24]=O.[C:32]([C:38]([O:40][CH3:41])=[O:39])#[C:33][C:34]([O:36][CH3:37])=[O:35]>>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:24]2[C:5]3[C:4](=[CH:9][C:8]([O:10][CH3:11])=[C:7]([O:12][CH3:13])[C:6]=3[O:14][CH3:15])[C:3]([OH:17])=[C:33]([C:34]([O:36][CH3:37])=[O:35])[C:32]=2[C:38]([O:40][CH3:41])=[O:39])[CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH3:31]

Participants

Reactant 3

HCID 12980Dimethyl acetylenedicarboxylate

HCID 671164-Ethoxy-3-methoxybenzaldehyde

HCID 159144582-Bromo-3,4,5-trimethoxybenzaldehyde dimethylacetal

Product 1

HCID 139108271-(3-Methoxy-4-ethoxyphenyl)-2,3-bis(methoxycarbonyl)-4-hydroxy-6,7,8-trimethoxynaphthaleneYield 67%

Procedure

2-Bromo-3,4,5-trimethoxybenzaldehyde dimethylacetal, 3-methoxy-4-ethoxybenzaldehyde and dimethyl acetylenedicarboxylate are treated in the same manner as described in Example 1, whereby 1-(3-methoxy-4-ethoxyphenyl)-2,3-bis(methoxycarbonyl)-4-hydroxy-6,7,8-trimethoxynaphthalene is obtained as colorless needles. Yield: 67%

Sources & evidence

ORD record: ord-68abce3b5cf34756a1620115ccb7ff85
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04771072

Linked notes

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