Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate → HCID 85471953, compound

HRID 2177352Notes

Reaction equation

C(C1C=CC(C2SC=CC=2CO)=CC=1)C.OC1C(F)=CC(CCC(OCC)=O)=CC=1F.[CH2:32]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[S:41][CH:42]=[CH:43][C:44]=2[CH2:45][O:46][C:47]2[C:52]([F:53])=[CH:51][C:50]([CH2:54][CH2:55][C:56]([O:58]CC)=[O:57])=[CH:49][C:48]=2[F:61])=[CH:36][CH:35]=1)[CH3:33]>>[CH2:32]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[S:41][CH:42]=[CH:43][C:44]=2[CH2:45][O:46][C:47]2[C:52]([F:53])=[CH:51][C:50]([CH2:54][CH2:55][C:56]([OH:58])=[O:57])=[CH:49][C:48]=2[F:61])=[CH:36][CH:35]=1)[CH3:33]

Participants

Reactant 3

HCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate

HCID 90418449HCID 90418449, compound

HCID 90418719HCID 90418719, compound

Product 1

HCID 85471953HCID 85471953, compound

Procedure

The title compound was prepared according to the procedure described in Example 207 by coupling of (2-(4-ethylphenyl)thiophen-3-yl)methanol and ethyl 3-(4-hydroxy-3,5-difluoro phenyl)propanoate followed by hydrolysis of ethyl 3-(4-((2-(4-ethylphenyl)thiophen-3-yl)methoxy)-3,5-difluorophenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 7.49 (d, J=6.5 Hz, 2H), 7.28 (m, 3H), 7.20 (m, 1H), 6.76 (d, J=6.5 Hz, 2H), 5.05 (s, 2H), 2.88 (t, J=6.0 Hz, 2H), 2.70 (m, 2H), 2.62 (t, J=6.0 Hz, 2H), 1.25 (t, J=7.5 Hz, 3H).

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-7ec81e93e5cc4b8794d5e4c5bb67c948
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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