Pyridine → (5-Bromopentyl)cyclohexane

HRID 654897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 654897
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.P(Br)(Br)[Br:20]>O1CCCC1>[Br:20][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 269450Cyclohexanepentanol

Produkt 1

HCID 14952366(5-Bromopentyl)cyclohexane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-cyclohexylpentanol (1.74 g., 10.25 mmol) and pyridine (0.94 g., 11.1 mmol) at 0° under argon was added phosphorus tribromide (1.21 g., 4.5 mmol) dropwise. The reaction mixture became viscous, therefore 25 ml tetrahydrofuran was added. This mixture was stirred for 1.5 hours at room temperature, then partitioned between ethyl ether and 5% aqueous hydrochloric acid. The organic portion was washed with a 5% sodium bicarbonate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a dark yellow oil. Purification by flash chromatography (silica, hexane) yielded the desired alkyl halide.

Aufarbeitung

  1. custompartitioned between ethyl ether and 5% aqueous hydrochloric acid
  2. washThe organic portion was washed with a 5% sodium bicarbonate solution, water, saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a dark yellow oil
  7. customPurification by flash chromatography (silica, hexane)

Quellen und Nachweise

ORD-Eintrag
ord-93b334b57cf84c8e8dca500a087d273c
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05134128

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