Methanesulfonyl chloride → HCID 178505328, Verbindung

HRID 432235

Reaktionsgleichung

Reaktionsgleichung von HRID 432235
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:13][C@H:12]([OH:14])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>N1C=CC=CC=1>[CH3:15][S:16]([O:14][C@H:12]1[CH2:13][C@@H:10]([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:11]1)(=[O:18])=[O:17]

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 178521634HCID 178521634, Verbindung

Produkt 1

HCID 178505328HCID 178505328, VerbindungAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of cis 3-((benzyloxy)methyl)-1-cyclobutanol (2.50 g, 0.0130 mol) in pyridine (50 mL) was cooled to 0° C. Methanesulfonyl chloride (1.21 mL, 1.79 g, 0.0126 mol) was added dropwise, keeping the temperature below 2° C. The mixture was stirred for four hours, and then poured into ice water (100 mL) and extracted with ethyl ether (2×50 mL). The combined organic layers were washed with water (3×50 mL) and brine (50 mL). The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo to give cis 3-[(benzyloxy)methyl]cyclobutyl methanesulfonate (2.73 g, 0.0101 mol) as a yellow oil.

Aufarbeitung

  1. customthe temperature below 2° C
  2. extractionextracted with ethyl ether (2×50 mL)
  3. washThe combined organic layers were washed with water (3×50 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-91c9504295d64c2281d150cf9ea34aaa
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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