Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → HCID 85472982, compound

HRID 2177332Notes

Reaction equation

ClC1SC(CO)=C(C2C=CC(Cl)=CC=2)C=1.OC1C=CC(CCC(OCC)=O)=C(C)C=1C.[Cl:32][C:33]1[S:37][C:36]([CH2:38][O:39][C:40]2[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][C:48]([O:50]CC)=[O:49])=[C:42]([CH3:53])[C:41]=2[CH3:54])=[C:35]([C:55]2[CH:60]=[CH:59][C:58]([Cl:61])=[CH:57][CH:56]=2)[CH:34]=1>>[Cl:32][C:33]1[S:37][C:36]([CH2:38][O:39][C:40]2[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][C:48]([OH:50])=[O:49])=[C:42]([CH3:53])[C:41]=2[CH3:54])=[C:35]([C:55]2[CH:60]=[CH:59][C:58]([Cl:61])=[CH:57][CH:56]=2)[CH:34]=1

Participants

Reactant 3

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

HCID 90418341HCID 90418341, compound

HCID 90418713HCID 90418713, compound

Product 1

HCID 85472982HCID 85472982, compound

Procedure

The title compound was prepared according to the procedure described in Example 197 by coupling of [5-chloro-3-(4-chlorophenyl)thiophen-2-yl]methanol and ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate followed by hydrolysis of ethyl 3-(4-((5-chloro-3-(4-chlorophenyl)thiophen-2-yl)methoxy)-2,3-dimethylphenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (300 MHz, CD3OD) δ 7.40 (s, 4H), 7.03 (s, 1H), 6.89 (d, J=8.4 Hz, 1H), 6.59 (d, J=8.4 Hz, 1H), 5.04 (s, 2H), 2.85 (t, J=5.1 Hz, 2H), 2.46 (t, J=5.1 Hz, 2H), 2.11 (s, 3H), 2.00 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C22H20Cl2O3S, 433.1 (M−H). found 433.1.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-be5626c9fda64660880826bb59386066
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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