3,4-dihydro-2H-pyran → 2-(5-Bromopentyloxy)tetrahydro-2H-pyran

HRID 471321

Reaktionsgleichung

Reaktionsgleichung von HRID 471321
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:25]1[CH:30]=[CH:29][CH2:28][CH2:27][CH2:26]1>C(Cl)Cl.CCOCC>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][O:25]1

Komponenten

6

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 1187091-Pentanol, 5-bromo-HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Produkt 1

HCID 27869332-(5-Bromopentyloxy)tetrahydro-2H-pyran

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-bromopentanol (10 g) in DCM (150 mL) was added pyridinium p-toluenesulfonate (1.5 g) followed by 3,4-dihydro-2H-pyran (8.1 mL) and the reaction mixture was stirred at room temperature under nitrogen for 21 hours. The solution was diluted with ether then washed with diluted brine (1:1 brine:water, 140 mL) before the organics were dried over sodium sulfate, filtered and evaporated. Purification was by silica gel chromatography eluting with 0 to 50% ethyl acetate in cyclohexane to afford the subtitled compound as a colourless liquid. Yield 14.14 g.

Aufarbeitung

  1. washthen washed with diluted brine (1:1 brine:water, 140 mL) before the
  2. dry with materialorganics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customPurification
  6. washeluting with 0 to 50% ethyl acetate in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-6a57973373d740f98d5cad8b22a4f64f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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