Ethyl 3-fluoro-4-hydroxybenzoate → 3-Fluoro-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzoic acid

Reaction equation

C([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([F:12])[CH:6]=1)C.[O:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[CH2:19]OS(C)(=O)=O>>[F:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[O:11][CH2:19][C@@H:15]1[CH2:16][CH2:17][CH2:18][O:14]1)[C:4]([OH:3])=[O:13]

Participants

Reactant 2

HCID 13745619Ethyl 3-fluoro-4-hydroxybenzoate

HCID 18649743(S)-1-(tetrahydrofuran-2-yl)methyl methanesulfonate

Product 1

HCID 286048713-Fluoro-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzoic acid

Procedure

According to method F, 3-fluoro-4-hydroxybenzoic acid ethyl ester was alkylated with methanesulfonic acid (S)-1-(tetrahydrofuran-2-yl)methyl ester, and the reaction product was hydrolyzed by method E. The product was thus obtained with the molecular weight of 240.23 (C12H13FO4); MS (ESI): 241 (M+H+).

Workup

customThe product was thus obtained with the molecular weight of 240.23 (C12H13FO4)

Sources & evidence

ORD record: ord-9332a8580de44b0785f302af0b42a027
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609731B2

Reaction notes

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