Triethylamine → 3-Nitrophenethyl methanesulfonate

HRID 15770

Reaktionsgleichung

Reaktionsgleichung von HRID 15770
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N+:6]([C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][OH:17])[CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7].C(N(CC)CC)C>ClCCl.O>[CH3:1][S:2]([O:17][CH2:16][CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([N+:6]([O-:8])=[O:7])[CH:10]=1)(=[O:4])=[O:3]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1040583-Nitrophenylethyl alcohol

Produkt 1

HCID 219738843-Nitrophenethyl methanesulfonateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methanesulfonyl chloride (0.28 mL) was added dropwise to a stirred solution of 2-(3-nitrophenyl)ethanol (0.5 g; 1 eq) in dichloromethane (3 mL) and triethylamine (0.5 mL; 1.2 eq) at 0° C. under an inert atmosphere. The solution was allowed to reach r.t. and stirred for 5 hours. The reaction mixture was diluted with water (3 mL) and extracted into dichloromethane (3×3 mL). The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by flash chromatography, eluting with a gradient from dichloromethane to dichloromethane/MeOH (98/2) affording the title compound in 84% yield (0.62 g).

Aufarbeitung

  1. customto reach r.t.
  2. extractionextracted into dichloromethane (3×3 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by flash chromatography
  6. washeluting with a gradient from dichloromethane to dichloromethane/MeOH (98/2)

Quellen und Nachweise

ORD-Eintrag
ord-b0d83144ac3a492fa8c9af88da90f448
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732600B2

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