3,4-dihydro-2H-pyran → 2-(4-Bromobutoxy)tetrahydro-2H-pyran

HRID 39246

Reaktionsgleichung

Reaktionsgleichung von HRID 39246
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.ClCCl>[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1

Komponenten

5

Edukt 2

HCID 80803,4-dihydro-2H-pyranHCID 1183884-Bromobutanol

Produkt 1

HCID 5590192-(4-Bromobutoxy)tetrahydro-2H-pyranAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3,4-Dihydro-2H-pyran (8.5 mL, 90.96 mmol) was added dropwise to the dichloromethane (20 mL) solution of 1 (10.7 g, 69.93 mmol) and p-toluenesulfonic acid monohydrate (26.5 mg, 0.1372 mmol). The mixture was stirred at room temperature over night. After removing the solvent, the residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent to yield product 2 as a colorless oil (15.3 g, 92%). 1H NMR (400 MHz, CDCl3): δ 1.48-1.62 (m, 4H), 1.68-1.85 (m, 4H), 1.94-2.02 (m, 2H), 3.40-3.53 (m, 4H), 3.74-3.88 (m, 2H), 4.57-4.59 (m, 1H).

Aufarbeitung

  1. customAfter removing the solvent
  2. customthe residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-4df15ee16ba343d6858c801aa90a4577
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524691B2

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