Triethylamine → Methanesulfonic acid 1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl ester

HRID 2169280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169280
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:14][OH:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.CCN(CC)CC.[S:25](Cl)([CH3:28])(=[O:27])=[O:26]>ClCCl>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2([CH2:14][O:15][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86725928[1-(4-Trifluoromethyl-phenyl)-cyclopentyl]-methanol

Produkt 1

HCID 86725929Methanesulfonic acid 1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl esterAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred of 1-(4-trifluoromethyl-phenyl)-cyclopentyl]-methanol (239) (15 g, 61.47 mmol) in dichloromethane (200 mL) was added Et3N (17.1 mL, 123 mmol) followed by mesyl chloride (5.7 mL, 73.77 mmol) dropwise at 0° C. The reaction mixture was stirred at room temperature for 1 h. After completion, the reaction was quenched by the addition of water. The reaction mixture was diluted with dichloromethane. The organic part was washed with water, separated, dried over Na2SO4 and finally concentrated. The crude product was purified by 100-200 silica column chromatography using 10% ethyl acetate in hexane as the eluent to give methanesulfonic acid 1-(4-trifluoromethyl-phenyl)-cyclopentylmethyl ester (240) (14 g, 70.6%) as a white solid.

Aufarbeitung

  1. customAfter completion, the reaction was quenched by the addition of water
  2. additionThe reaction mixture was diluted with dichloromethane
  3. washThe organic part was washed with water
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. concentrationfinally concentrated
  7. customThe crude product was purified by 100-200 silica column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-114586647b7d4f008c393d4051bc9cd1
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045486B2

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