Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → 3-(4-((3-(4-Ethylphenyl)-5-methylthiophen-2-yl)methoxy)-2,3-dimethylphenyl)propanoic acid

HRID 2177347Notes

Reaction equation

HRID 2177347 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([CH3:14])[S:11][C:10]=2[CH2:15][OH:16])=[CH:5][CH:4]=1)[CH3:2].O[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])=[C:20]([CH3:31])[C:19]=1[CH3:32].C(C1C=CC(C2C=C(C)SC=2COC2C(F)=CC(CCC(OCC)=O)=CC=2F)=CC=1)C>>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:13]=[C:12]([CH3:14])[S:11][C:10]=2[CH2:15][O:16][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[C:20]([CH3:31])[C:19]=2[CH3:32])=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 3

HCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 90418314(3-(4-Ethylphenyl)-5-methylthiophen-2-yl)methanolHCID 90418817Ethyl 3-(4-((3-(4-ethylphenyl)-5-methylthiophen-2-yl)methoxy)-3,5-difluorophenyl)propanoate

Product 1

HCID 854731033-(4-((3-(4-Ethylphenyl)-5-methylthiophen-2-yl)methoxy)-2,3-dimethylphenyl)propanoic acid

Procedure

The title compound was prepared according to the procedure described in Example 207 by coupling of (3-(4-ethylphenyl)-5-methylthiophen-2-yl)methanol and ethyl 3-(4-hydroxy-2,3-dimethyl phenyl)propanoate followed by hydrolysis of ethyl 3-(4-((3-(4-ethylphenyl)-5-methylthiophen-2-yl)methoxy)-3,5-difluorophenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.35 (d, J=7.5 Hz, 2H), 7.26 (s, 1H), 7.18 (d, J=7.5 Hz, 2H), 6.95 (d, J=7.0 Hz, 1H), 6.64 (d, J=7.1 Hz, 1H), 5.05 (s, 2H), 2.95 (t, J=6.5 Hz, 2H), 2.68 (m, J=7.5 Hz, 2H), 2.58 (t, J=6.2 Hz, 2H), 2.51 (s, 3H), 2.21 (s, 3H), 2.20 (s, 3H), 1.26 (t, J=8.0 Hz, 3H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-f5e77f251b2e4eac9363866bbb6281cc
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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