2-Dimethylaminopyridine → 2,3-Dihydro-1h-inden-2-yl methanesulfonate

HRID 450726

Reaktionsgleichung

Reaktionsgleichung von HRID 450726
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[OH:10].C(N(C(C)C)CC)(C)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].CN(C1C=CC=CN=1)C>ClCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][S:21]([CH3:20])(=[O:23])=[O:22]

Komponenten

6

Edukt 4

HCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 779362-IndanolHCID 81531Diisopropylethylamine

Produkt 1

HCID 2552212,3-Dihydro-1h-inden-2-yl methanesulfonateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Indanol (20.00 g, 149.5 mmol) and diisopropylethylamine (21.2 g, 164 mmol) was stirred in dichloromethane (300 mL) at 0° C. Methanesulfonyl chloride (18.78 g, 164 mmol) and dimethylaminopyridine (1.80 g) were added simultaneously and stirring continued at room temperature for 18 h. Solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated. This was washed with NaHCO3 (sat) and with citric acid solution (5%) and dried over MgSO4. The filtered solution was concentrated and the resultant solid recrystallized from isopropanol-EtOH (3:1) to give off-white crystals (24.6 g, 78%).

Aufarbeitung

  1. customSolution was evaporated
  2. custompartitioned between ethyl acetate and water
  3. customthe organic phase separated
  4. washThis was washed with NaHCO3 (sat) and with citric acid solution (5%)
  5. dry with materialdried over MgSO4
  6. concentrationThe filtered solution was concentrated
  7. customthe resultant solid recrystallized from isopropanol-EtOH (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-8a773c1aeae7433abb88a6f5b83d4413
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486984B2

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