Acetic Acid → 3-[1-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl-benzoic acid

HRID 1628194Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628194
ClC(Cl)(Cl)COC(=O)[C:6]1[CH:11]=[CH:10][CH:9]=C[C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:15]=1.[CH3:39][C:40]([OH:42])=[O:41].C(Cl)Cl>CCCCCCC.CCOC(C)=O.[Zn]>[F:29][C:27]([F:28])([F:30])[C:24]1[CH:23]=[CH:22][C:21]([CH:20]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:16]2[C:15]([CH2:14][S:13][C:12]3[CH:7]=[CH:6][CH:11]=[CH:10][CH:9]=3)=[C:39]([CH:19]=[CH:18][CH:17]=2)[C:40]([OH:42])=[O:41])=[CH:26][CH:25]=1

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 866503112-{3-[1-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl}-benzoic acid 2,2,2-trichloro-ethyl ester

Produkt 1

HCID 866551303-[1-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl-benzoic acidAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

The titled compound was prepared according to the method described for example 1 above from 2-{3-[1-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl}-benzoic acid 2,2,2-trichloro-ethyl ester (157 mg, 0.0.259 mmol), zinc (339 mg, 5.18 mmol), HOAc, 97% (1.48 mL, 25.9 mmol) and DCM (12 mL). The crude was submitted to flash chromatography using heptane and EtOAc (70/30-60/40) as eluent to give the titled compound (94 mg, 77%) as an oil; 1H NMR (400 MHz, CDCl3): δ 1.53 (s, 3H), 3.60 (dd, 2H), 4.54 (dd, 2H), 5.91 (m, 1H), 7.07-7.12 (m, 1H), 7.15-7.20 (m, 2H), 7.21-7.32 (m, 3H), 7.35-7.42 (m, 3H), 7.58 (d, 2H), 7.98 (d, 1H); Mass spectrum: M−H+ 473.

Aufarbeitung

  1. customThe titled compound was prepared

Quellen und Nachweise

ORD-Eintrag
ord-28d2e3f994ae4ca1b839d811e41cf32d
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785681B2

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