Triethylamine → HCID 86697766, Verbindung

HRID 2279829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2279829
[CH2:1]([O:8][CH2:9][C:10]1([CH2:14][OH:15])[CH2:13][O:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([O:15][CH2:14][C:10]1([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][O:12][CH2:11]1)(=[O:26])=[O:25]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20063122(3-((Benzyloxy)methyl)oxetan-3-yl)methanol

Produkt 1

HCID 86697766HCID 86697766, VerbindungAusbeute 523,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

An ice cooled solution of (3-(benzyloxymethyl)oxetan-3-yl)methanol (Example 44E, 1.00 g, 4.80 mmol) in DCM (5.14 mL) was treated with triethylamine (1.31 mL, 9.43 mmol) and methanesulfonyl chloride (0.438 mL, 5.66 mmol) and gradually allowed to warm up to rt over 16 hrs. The mixture was diluted with DCM, washed with saturated aqueous NaHCO3 solution (1×), brine (2×), dried over anhydrous sodium sulfate, filtered, concentrated in vacuo to a solid to afford 7.2 g of the title compound (100%). The crude product was used in next step without further purification. 1H NMR (400 MHz, CD3OD) δ 7.23-7.38 (m, 5H), 4.58 (s, 2H), 4.46-4.54 (m, 6H), 3.74 (s, 2H), 3.09 (s, 3H).

Aufarbeitung

  1. washwashed with saturated aqueous NaHCO3 solution (1×), brine (2×)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a solid

Quellen und Nachweise

ORD-Eintrag
ord-ec4f16da38ed4709bc8b95f3850f12df
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133224B2

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