Diethyl acetylenedicarboxylate → 1-(3,4-Dimethoxyphenyl)-2,3-bis(ethoxycarbonyl)-4-hydroxy-6,7,8-trimethoxynaphthalene

HRID 974113Notes

Reaction equation

C[O:2][CH:3](OC)[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]=1[CH:16](O)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1.[C:30]([C:37]([O:39][CH2:40][CH3:41])=[O:38])#[C:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>>[CH3:26][O:25][C:19]1[CH:18]=[C:17]([C:16]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:2])=[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:30]=2[C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:22]=[CH:21][C:20]=1[O:23][CH3:24]

Participants

Reactant 2

HCID 69803Diethyl acetylenedicarboxylate

HCID 105975732-(3,4-Dimethoxy-alpha-hydroxybenzyl)-3,4,5-trimethoxybenzaldehyde dimethyl acetal

Product 1

HCID 105777341-(3,4-Dimethoxyphenyl)-2,3-bis(ethoxycarbonyl)-4-hydroxy-6,7,8-trimethoxynaphthaleneYield 43%

Procedure

40.8 g of 2-(3,4-dimethoxy-α-hydroxybenzyl)-3,4,5-trimethoxybenzaldehyde dimethyl acetal and 17.0 g of diethyl acetylenedicarboxylate are treated in the same manner as described in Example 1-(3) to give 1-(3,4-dimethoxyphenyl)-2,3-bis(ethoxycarbonyl)-4-hydroxy-6,7,8-trimethoxynaphthalene. Yield: 43%

Sources & evidence

ORD record: ord-395c83d067ab4b17a3698f7cde4e9347
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05066825

Reaction notes

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