Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → HCID 85472979, compound

HRID 2177340Notes

Reaction equation

HRID 2177340 reaction equation
ClC1C=CC(C2C=C(F)SC=2CO)=CC=1.OC1C=CC(CCC(OCC)=O)=C(C)C=1C.[F: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:61][C:58]1[CH:59]=[CH:60][C:55]([C:35]2[CH:34]=[C:33]([F:32])[S:37][C:36]=2[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])=[CH:56][CH:57]=1

Participants

4

Reactant 3

HCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 90418004HCID 90418004, compoundHCID 90418188HCID 90418188, compound

Product 1

HCID 85472979HCID 85472979, compound

Procedure

The title compound was prepared according to the procedure described in Example 202 by coupling of [3-(4-chlorophenyl)-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-chlorophenyl)thiophen-2-yl)methoxy)-2,3-dimethylphenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=8.0 Hz, 2H), 7.30 (d, J=8.0 Hz, 2H), 6.95 (d, J=7.1 Hz, 1H), 6.62 (d, J=7.1 Hz, 1H), 6.51 (s, 1H), 4.98 (s, 2H), 2.97 (t, J=7.5 Hz, 2H), 2.68 (t, J=7.5 Hz, 2H), 2.28 (s, 3H), 2.21 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C22H20ClFO3S, 417.1 (M−H). found 417.1.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-bbb99e07eecd457a9156059fe627b912
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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