Water → 2-(3-Butynyloxy)tetrahydro-2H-pyran

HRID 17187

Reaktionsgleichung

Reaktionsgleichung von HRID 17187
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>ClCCl>[CH2:1]([O:5][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1)[CH2:2][C:3]#[CH:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 135663-Butyn-1-OLHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Produkt 1

HCID 1424402-(3-Butynyloxy)tetrahydro-2H-pyranAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of but-3-yn-1-ol (10.00 g, 143 mmol) in dichloromethane (310 mL) was treated with dihyropyran (18.10 g, 215 mmol) and pyridinium p-toluene sulfonate (3.60 g, 14.30 mmol). The reaction mixture was stirred at room temperature for 4 days. Water was added and the layers were partitioned. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The crude material was purified by flash chromatography on silica gel using 1:1 ethyl acetate: heptane to give 21.57 g (98%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ 4.65 (m, 1H), 3.90-3.80 (m, 2H), 3.60-3.50 (m, 2H), 2.50-2.45 (m, 2H), 1.95 (m, 1H), 1.90-1.80 (m, 1H), 1.79-1.10 (m, 1H), 1.65-1.50 (m, 4H).

Aufarbeitung

  1. customthe layers were partitioned
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude material was purified by flash chromatography on silica gel using 1:1 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-450e4f1abcb741528cf798f1cb8baa32
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737160B2

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