Tetrahydrofuran → trans-(2-(((Tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methyl methanesulfonate

HRID 2202261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202261
[Si:1]([O:18][CH2:19][C@@H:20]1[CH2:22][C@H:21]1[CH2:23][OH:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].C1COCC1>O>[CH3:25][S:26]([O:24][CH2:23][C@@H:21]1[CH2:22][C@H:20]1[CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:28])=[O:27]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 10042906trans-(2-((Tert-butyldiphenylsilyloxy)methyl)cyclopropyl)methanol

Produkt 1

HCID 10025044trans-(2-(((Tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methyl methanesulfonateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

TEA (0.450 mL, 3.23 mmol) was added to a mixture of trans-(2-((tert-butyldiphenylsilyloxy)methyl)cyclopropyl)methanol (1 g, 2.94 mmol), methanesulfonyl chloride (0.250 mL, 3.23 mmol) and THF (10 mL) at 0° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give trans-(2-(((tert-butyldiphenylsilyl)oxy)methyl)cyclopropyl)methyl methanesulfonate (1.230 g, 2.94 mmol, 100%) as a colorless oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-205e3c611ce84a34b53fb074622e9c7b
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365520B2

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