3,4-dihydro-2H-pyran → Methyl 3-(oxan-2-yloxy)propanoate

HRID 1749685

Reaktionsgleichung

Reaktionsgleichung von HRID 1749685
[OH:1][CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1>ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:1][CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5]

Komponenten

5

Edukt 2

HCID 80803,4-dihydro-2H-pyranHCID 80252Propanoic acid, 3-hydroxy-, methyl ester

Produkt 1

HCID 15614101Methyl 3-(oxan-2-yloxy)propanoateAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Pyridinium p-toluenesulfonate (7.65 g, 30.45 mmol) was added to a clear solution of methyl 3-hydroxypropanoate (63.4 g, 609.00 mmol) and 3,4-dihydro-2H-pyran (78 mL, 852.60 mmol) in dichloromethane (650 mL) at room temperature under nitrogen to give a cloudy solution. This was allowed to stir at room temperature overnight. The reaction mixture was washed with water (250 mL) and brine (250 mL) before drying (MgSO4) and evaporating to an oil. This crude product was purified by flash silica chromatography, elution gradient 15 to 30% EtOAc in heptane. Pure fractions were evaporated to dryness to afford methyl 3-(tetrahydro-2H-pyran-2-yloxy)propanoate (67.7 g, 59.0%) as a colourless oil: 1H NMR Spectrum: (CDCl3) 1.47 (4H, dddd), 1.55-1.84 (2H, m), 2.55 (2H, t), 3.33-3.53 (1H, m), 3.53-3.7 (4H, m), 3.78 (1H, ddd), 3.93 (1H, dt), 4.42-4.72 (1H, m); Mass Spectrum [MH]+=189.

Aufarbeitung

  1. customto give a cloudy solution
  2. washThe reaction mixture was washed with water (250 mL) and brine (250 mL)
  3. dry with materialbefore drying (MgSO4)
  4. customevaporating to an oil
  5. customThis crude product was purified by flash silica chromatography, elution gradient 15 to 30% EtOAc in heptane
  6. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-5257f926bd704cdaad71642236d2430f
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156831B2

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