Water → 2-[2-[2-(Phenylmethoxy)ethoxy]ethyl]pyridine

HRID 2108134

Reaktionsgleichung

Reaktionsgleichung von HRID 2108134
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][OH:11].CS(O[CH2:17][CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=O)=O.O>COCCOC>[C:21]1([CH2:20][O:19][CH2:18][CH2:17][O:11][CH2:10][CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 76752-(2-Hydroxyethyl)pyridineHCID 24758Sodium hydrideHCID 108572722-Benzyloxyethyl mesylate

Produkt 1

HCID 230452622-[2-[2-(Phenylmethoxy)ethoxy]ethyl]pyridineAusbeute 29,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

Sodium hydride (80% dispersion in oil, 1.68 g) was added portionwise to a solution of 2-pyridineethanol (6.88 g) in 1,2-dimethoxyethane (50 ml) and stirred under nitrogen for 18 h at room temperature. A solution of 2-(phenylmethoxy)ethanol methanesulphonate (8.25 g) in 1,2-dimethoxyethane (100 ml) was added and the mixture stirred at room temperature for 7 h, then poured into water (400 ml) and extracted with diethyl ether (3×200 ml). The ethereal extracts were washed with 2N hydrochloric acid (250 ml). The aqueous phase was re-extracted with diethyl ether (100 ml) and the aqueous phase carefully basified with 8% sodium bicarbonate to pH8. Extraction with diethyl ether (2×200 ml) and drying and evaporation in vacuo of the organic extracts gave an oil. Purification by FCC eluting with System F (4.1→1.1) gave the title compound (2.71 g) as an oil. T.l.c. (diethyl ether) Rf 0.54

Aufarbeitung

  1. stirringthe mixture stirred at room temperature for 7 h
  2. extractionextracted with diethyl ether (3×200 ml)
  3. washThe ethereal extracts were washed with 2N hydrochloric acid (250 ml)
  4. extractionThe aqueous phase was re-extracted with diethyl ether (100 ml)
  5. extractionExtraction with diethyl ether (2×200 ml)
  6. customdrying
  7. customevaporation in vacuo of the organic extracts
  8. customgave an oil
  9. customPurification by FCC
  10. washeluting with System F (4.1→1.1)

Quellen und Nachweise

ORD-Eintrag
ord-b6db2bf2d5a44755af3efe74aa28002b
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04937268

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