Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → HCID 85472863, compound

HRID 2177341Notes

Reaction equation

C(C1C=CC(C2C=C(F)SC=2CO)=CC=1)C.OC1C=CC(CCC(OCC)=O)=C(C)C=1C.[F:33][C:34]1[S:38][C:37]([CH2:39][O:40][C:41]2[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][C:49]([O:51]CC)=[O:50])=[C:43]([CH3:54])[C:42]=2[CH3:55])=[C:36]([C:56]2[CH:61]=[CH:60][C:59]([CH2:62][CH3:63])=[CH:58][CH:57]=2)[CH:35]=1>>[CH2:62]([C:59]1[CH:58]=[CH:57][C:56]([C:36]2[CH:35]=[C:34]([F:33])[S:38][C:37]=2[CH2:39][O:40][C:41]2[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][C:49]([OH:51])=[O:50])=[C:43]([CH3:54])[C:42]=2[CH3:55])=[CH:61][CH:60]=1)[CH3:63]

Participants

Reactant 3

HCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate

HCID 90418810HCID 90418810, compound

HCID 90418821HCID 90418821, compound

Product 1

HCID 85472863HCID 85472863, compound

Procedure

The title compound was prepared according to the procedure described in Example 196 by coupling of [3-(4-ethylphenyl)-5-fluorothiophen-2-yl]methanol and ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate followed by hydrolysis of ethyl 3-(4-((5-fluoro-3-(4-ehtylphenyl)thiophen-2-yl)methoxy)-2,3-dimethylphenyl)propanoate to afford the desired product as an off-white solid. 1H-NMR (300 MHz, CD3OD) δ 7.34 (d, J=8.1 Hz, 2H), 7.26 (d, J=8.1 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 6.62-6.64 (m, 2H), 5.05 (s, 2H), 2.89 (t, J=8.1 Hz, 2H), 2.65-2.72 (m, 2H), 2.49 (d, J=8.1 Hz, 2H), 2.24 (s, 3H), 2.21 (s, 3H), 1.29 (t, J=7.5 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C24H25FO3S, 411.2 (M−H). found 411.2.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-d74a08fc52d34f55b872bd9ea6bb4528
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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