3,4,5-Trimethoxybenzaldehyde → HCID 323473, compound

HRID 1153818Notes

Reaction equation

HRID 1153818 reaction equation
[C:1]1(=[O:6])[O:5][CH2:4][CH:3]=[CH:2]1.[S:7]1[CH2:12][CH2:11][CH2:10][S:9][CH2:8]1.[CH:13]1[C:18]([CH:19]=O)=[CH:17][C:16]2[O:21][CH2:22][O:23][C:15]=2[CH:14]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35])C=O>>[CH3:37][O:36][C:32]1[C:33]([O:34][CH3:35])=[C:26]([O:25][CH3:24])[CH:27]=[C:28]([CH:19]2[C:18]3[C:13](=[CH:14][C:15]4[O:23][CH2:22][O:21][C:16]=4[CH:17]=3)[C:8]3([S:9][CH2:10][CH2:11][CH2:12][S:7]3)[CH:3]3[CH2:4][O:5][C:1](=[O:6])[CH:2]23)[CH:31]=1

Participants

5

Reactant 4

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 8438PiperonalHCID 103412(5H)-FuranoneHCID 104511,3-Dithiane

Product 1

HCID 323473HCID 323473, compound

Procedure

This step in the process parallels work disclosed by Ziegler, et al., J. Org. Chem. 43: 985-991 (1978), in which 2-butenolide was added to a 1,3-dithiane derivative of piperonal and subsequently reacted with 3,4,5-trimethoxybenzaldehyde to produce (±) -isopodophyllotoxone dithiane.

Sources & evidence

ORD record
ord-b4edb7a864604661a2bea407c8673558
Source dataset
uspto-grants-1984_12
Patent number
US04486445

Reaction notes

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