Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → HCID 85472088, compound

HRID 2177368Notes

Reaction equation

C(C1C=CC(C2SC(C)=C(C(F)(F)F)C=2CO)=CC=1)C.OC1C=CC(CCC(OCC)=O)=C(C)C=1C.[CH2:37]([C:39]1[CH:44]=[CH:43][C:42]([C:45]2[S:46][C:47]([CH3:71])=[C:48]([C:67]([F:70])([F:69])[F:68])[C:49]=2[CH2:50][O:51][C:52]2[CH:57]=[CH:56][C:55]([CH2:58][CH2:59][C:60]([O:62]CC)=[O:61])=[C:54]([CH3:65])[C:53]=2[CH3:66])=[CH:41][CH:40]=1)[CH3:38]>>[CH2:37]([C:39]1[CH:40]=[CH:41][C:42]([C:45]2[S:46][C:47]([CH3:71])=[C:48]([C:67]([F:69])([F:68])[F:70])[C:49]=2[CH2:50][O:51][C:52]2[CH:57]=[CH:56][C:55]([CH2:58][CH2:59][C:60]([OH:62])=[O:61])=[C:54]([CH3:65])[C:53]=2[CH3:66])=[CH:43][CH:44]=1)[CH3:38]

Participants

Reactant 3

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

HCID 90418140HCID 90418140, compound

HCID 90418454HCID 90418454, compound

Product 1

HCID 85472088HCID 85472088, compound

Procedure

The title compound was prepared according to the procedure described in Example 220 by coupling of [2-(4-ethylphenyl)-5-methyl-4-(trifluoromethyl)thiophen-3-yl]methanol and ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate followed by hydrolysis of ethyl 3-(4-((2-(4-ethyl phenyl)-5-methyl-4-(trifluoromethyl)thiophen-3-yl)methoxy)-2,3-dimethylphenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (300 MHz, CDCl3) δ: 7.43 (d, J=4.2 Hz, 2H), 7.24 (d, J=6.0 Hz, 2H), 6.97 (d, J=6.3 Hz, 2H), 6.67 (d, J=6.3 Hz, 2H), 4.86 (s, 2H), 2.97 (t, J=6.0 Hz, 2H), 2.61-2.73 (m, 7H) 2.23 (s, 3H), 2.18 (s, 3H), 1.27 (t, J=5.7 Hz, 2H). Mass spectrum (ESI, m/z): Calcd. for C26H27F3O3S, 475.2[M−H]. found 475.2.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-ccb95813668d411cba1415efd6ca4132
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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