Methyl 3-cyano-3-(4-hydroxyphenyl)propanoate → 3-cyano-3-[4-[[4-[(2Z)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-methoxyiminoethoxy]phenyl]methoxy]phenyl]propanoic acid

HRID 922289Notes

Reaction equation

HRID 922289 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](/[C:10](=[N:21]/[O:22][CH3:23])/[CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][CH:14]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:24]([CH:26]([C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1)[CH2:27][C:28]([O:30]C)=[O:29])#[N:25]>>[C:24]([CH:26]([C:32]1[CH:37]=[CH:36][C:35]([O:20][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11]/[C:10](/[C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][CH2:3][C:4]=4[CH:9]=3)=[N:21]\[O:22][CH3:23])=[CH:14][CH:15]=2)=[CH:34][CH:33]=1)[CH2:27][C:28]([OH:30])=[O:29])#[N:25]

Participants

3

Reactant 2

HCID 66685605Methyl 3-cyano-3-(4-hydroxyphenyl)propanoateHCID 89790402[4-[(2Z)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-methoxyiminoethoxy]phenyl]methanol

Product 1

HCID 566396253-cyano-3-[4-[[4-[(2Z)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-methoxyiminoethoxy]phenyl]methoxy]phenyl]propanoic acidYield 56.2%

Procedure

Compound 102 was synthesized from ((4-{[(2Z)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-(methoxyimino)ethyl]oxy}phenyl)methanol (0.330 g, 1.0 mmol) and methyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.216 g, 1.0 mmol) by following the procedure described in scheme 5 (0.008 g, yield: 56.2%); Purity: 94.55%.

Sources & evidence

ORD record
ord-47f2dd061f914979be20225fcf54af14
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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