Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → HCID 90418407, compound

HRID 2177356Notes

Reaction equation

C(C1C=CC(C2C=C(C(F)(F)F)SC=2CO)=CC=1)C.OC1C=CC(CCC(OCC)=O)=C(C)C=1C.[CH2:36]([C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:48]=[C:47]([C:49]([F:52])([F:51])[F:50])[S:46][C:45]=2[CH2:53][O:54][C:55]2[CH:60]=[CH:59][C:58]([CH2:61][CH2:62][C:63]([O:65]CC)=[O:64])=[C:57]([CH3:68])[C:56]=2[CH3:69])=[CH:40][CH:39]=1)[CH3:37]>>[CH2:36]([C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:48]=[C:47]([C:49]([F:51])([F:52])[F:50])[S:46][C:45]=2[CH2:53][O:54][C:55]2[CH:60]=[CH:59][C:58]([CH2:61][CH2:62][C:63]([OH:65])=[O:64])=[C:57]([CH3:68])[C:56]=2[CH3:69])=[CH:40][CH:39]=1)[CH3:37]

Participants

Reactant 3

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

HCID 90418009HCID 90418009, compound

HCID 90418258HCID 90418258, compound

Product 1

HCID 90418407HCID 90418407, compound

Procedure

The title compound was prepared according to the procedure described in Example 208 by coupling of (3-(4-ethylphenyl)-5-(trifluoromethyl)thiophen-2-yl)methanol and ethyl 3-(4-hydroxy-2,3-dimethyl phenyl)propanoate followed by hydrolysis of ethyl 3-(4-((3-(4-ethylphenyl)-5-(trifluoromethyl)thiophen-2-yl)methoxy)-2,3-dimethylphenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.46 (s, 1H), 7.35 (d, J=6.0 Hz, 2H), 7.28 (d, J=6.0 Hz, 2H), 6.95 (d, J=5.3 Hz, 1H), 6.65 (d, J=5.3 Hz, 1H), 5.15 (s, 2H), 2.96 (t, J=5.5 Hz, 2H), 2.68 (q, J=5.5 Hz, 2H), 2.60 (t, J=6.0 Hz, 2H), 2.25 (s, 3H), 2.18 (s, 3H), 1.28 (t, J=7.0 Hz, 3H).

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-0f1f05d5cbdb4468bca1d5eccbd0eaa4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

Loading…