Methanesulfonyl chloride → HCID 86650639, Verbindung

HRID 1623392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1623392
[CH3:1][C:2]1([CH3:10])[O:7][CH:6]([CH2:8][OH:9])[CH2:5][O:4][CH2:3]1.[CH3:11][S:12](Cl)(=[O:14])=[O:13].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:11][S:12]([O:9][CH2:8][CH:6]1[CH2:5][O:4][CH2:3][C:2]([CH3:10])([CH3:1])[O:7]1)(=[O:14])=[O:13]

Komponenten

5

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 66937181(6,6-Dimethyl-1,4-dioxan-2-yl)methanol

Produkt 1

HCID 86650639HCID 86650639, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

TEA (0.52 mL, 3.74 mmol) and (6,6-dimethyl-1,4-dioxan-2-yl)methanol (390 mg, 2.67 mmol) were dissolved in DCM (10 mL). Methanesulfonyl chloride (0.249 mL, 3.20 mmol) was slowly added at 0° C. After the addition was completed the solution was warmed to ambient temperature and stirred for 1 hr. Saturated NaHCO3 solution was added and the two layers were separated. The aqueous layer was extracted three times with DCM. The organic layers were combined, dried over Na2SO4 and concentrated. The resulting residue was purified on a silica gel column (heptane:EtOAc 4:1 to 1:1) to give the product as a colorless oil (584 mg, 98%). 1H NMR (400 MHz, CDCl3) δ ppm 4.00-4.09 (3H, m), 3.74 (1H, dd, J=11.2, 2.8 Hz), 3.42 (1H, d, J=11.6 Hz), 3.16-3.23 (2H, m), 2.99 (3H, s), 1.27 (3H, s), 1.05 (3H, s).

Aufarbeitung

  1. additionAfter the addition
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted three times with DCM
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified on a silica gel column (heptane:EtOAc 4:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4758fe2eb511498a9540587c09ddb5fb
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778951B2

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