3,4-Dimethoxybenzeneacetonitrile → HCID 23089835, compound

HRID 2222370Notes

Reaction equation

HRID 2222370 reaction equation
[F:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16]Cl.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:23][C:24]#[N:25]>>[CH3:18][O:19][C:20]1[CH:21]=[C:22](/[C:23](=[CH:5]/[C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[C:3]=2[O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])/[C:24]#[N:25])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]

Participants

4

Reactant 3

HCID 667273,4-DimethoxybenzeneacetonitrileHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 5877883-Fluorosalicylaldehyde

Product 1

HCID 23089835HCID 23089835, compoundYield 62.2%

Procedure

The hydroxyl group of 3-fluoro-2-hydroxybenzaldehyde (560 mg) was protected by use of 2-methoxyethoxymethyl chloride (500 mg) in accordance with (production process 1), to thereby produce an MEM form (660 mg, yield: 72%). The resultant MEM form (650 mg) and 3,4-dimethoxybenzyl cyanide (500 mg) were subjected to condensation in accordance with process A of (production process 2), to thereby produce (Z)-2-(3,4-dimethoxy-phenyl)-3-(3-fluoro-2-methoxyethoxymethoxy-phenyl)-acrylonitrile (680 mg, yield: 58%). The thus-produced (Z)-2-(3,4-dimethoxy-phenyl)-3-(3-fluoro-2-methoxyethoxymethoxy-phenyl)-acrylonitrile (670 mg) was subjected to deprotection in accordance with (production process 3), to therey produce the target product (140 mg, yield: 29%).

Workup

  1. customto thereby produce an MEM form (660 mg, yield: 72%)

Sources & evidence

ORD record
ord-c62dc3868ebd4b1f85190b926c8e9e00
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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