Methanesulfonyl chloride → Methanesulfonyloxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester

HRID 77025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77025
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([OH:16])[C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:2].CCN(C(C)C)C(C)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([O:16][S:28]([CH3:27])(=[O:30])=[O:29])[C:6]1[CH:7]=[CH:8][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:10][CH:11]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 20286794Hydroxy 4-(trifluoromethyl)phenylacetic acid ethyl ester

Produkt 1

HCID 59401272Methanesulfonyloxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl esterAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Hydroxy-(4-trifluoromethyl-phenyl)-acetic acid ethyl ester (I101) (440 mg, 1.77 mmol) and DIPEA (0.43 mL, 2.48 mmol) are dissolved in dry DCM (17 mL) and cooled at 0° C. under N2. Methansulfonyl chloride (0.18 mL, 2.30 mmol) is added dropwise to the solution and the resulting mixture is allowed to warm to RT and stirred for 3 hours. The mixture is diluted with DCM and washed with sat. NaHCO3, water and brine. The organic layer is dried (Na2SO4), filtered and evaporated to obtain intermediate I150 as a yellow oil (578 mg, quantitative yield), which is used in the next step without any further purification.

Aufarbeitung

  1. temperatureto warm to RT
  2. washwashed with sat. NaHCO3, water and brine
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5f253bf3286f40bab843f3e034b780fd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835682B2

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