Syringaldehyde → HCID 23089858, compound

HRID 2222385Notes

Reaction equation

HRID 2222385 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:12][CH3:13].[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19]Cl.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:26][C:27]#[N:28]>>[CH3:13][O:12][C:3]1[CH:4]=[C:5](/[CH:6]=[C:26](/[C:25]2[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:23]([O:22][CH3:21])[CH:24]=2)\[C:27]#[N:28])[CH:8]=[C:9]([O:10][CH3:11])[C:2]=1[O:1][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19]

Participants

4

Reactant 3

HCID 8655SyringaldehydeHCID 667273,4-DimethoxybenzeneacetonitrileHCID 775901-(Chloromethoxy)-2-methoxyethane

Product 1

HCID 23089858HCID 23089858, compoundYield 65.3%

Procedure

The hydroxyl group of 4-hydroxy-3,5-dimethoxybenzaldehyde (2.44 g) was protected by use of 2-methoxyethoxymethyl chloride (1.67 g) in accordance with (production process 1), to thereby produce an MEM form (3.40 g, yield: 94%). The resultant MEM form (3.40 g) and 3,4-dimethoxybenzyl cyanide (2.23 g) were subjected to condensation in accordance with process A of (production process 2), to thereby produce (Z)-3-[3,5-dimethoxy-4-(2-methoxyethoxymethoxy)-phenyl]-2-(3,4-dimethoxy-phenyl)-acrylonitrile (3.53 g, yield: 65%). The thus-produced (Z)-3-[3,5-dimethoxy-4-(2-methoxyethoxymethoxy)-phenyl]-2-(3,4-dimethoxy-phenyl)-acrylonitrile (0.35 g) was subjected to deprotection in accordance with (production process 3), to thereby produce the target product (0.25 g, yield: 90%).

Workup

  1. customto thereby produce an MEM form (3.40 g, yield: 94%)

Sources & evidence

ORD record
ord-8ca6ffea869d49a09be297c7c285d9ea
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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