4-Penten-1-OL → 2-Pyridinepentanol

HRID 245130

Reaktionsgleichung

Reaktionsgleichung von HRID 245130
C12BC(CCC1)CCC2.[CH2:10]([OH:15])[CH2:11][CH2:12][CH:13]=[CH2:14].Cl.Br[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1>O1CCCC1.O.CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[K+].[K+]>[N:21]1[CH:22]=[CH:23][CH:18]=[CH:19][C:20]=1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][OH:15]

Komponenten

8

Edukt 3

HCID 131814-Penten-1-OLHCID 789669-Borabicyclo(3.3.1)nonaneHCID 881004-Bromopyridinium chloride

Produkt 1

HCID 143474782-PyridinepentanolAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 8028TetrahydrofuranLösungsmittelHCID 11430Potassium CarbonateLösungsmittelHCID 21962138N,N-Dimethylformamide--water (1/1)LösungsmittelHCID 178418397HCID 178418397, VerbindungLösungsmittel

Versuchsvorschrift

9-Borabicyclo[3.3.1]nonane (9-BBN) dissolved in 15 ml of tetrahydrofuran (manufactured by Aldrich Co.) was added to 300 mg (3.483 mmol) of 4-pentene-1-ol and allowed to react at 25° C. for 24 hours. Then, 4-bromopyridine hydrochloride (manufactured by Aldrich Co.) dissolved in water/dimethylformamide (DMF) at a ratio of 2:8, tetrakis(triphenylphosphine)palladium (manufactured by Aldrich Co.), and potassium carbonate (manufactured by Aldrich Co.) were added thereto in an equivalent ratio of 1:1.2:0.2 and allowed to react at 70° C. for 6 hours. Then, solvent was removed under reduced pressure, and the residual material was diluted with ethyl acetate and filtered with Celite. The material thus obtained was purified by column chromatography (column: silica (manufactured by Aldrich Co.), solvent: ethyl acetate/hexane) to obtain 203 mg of pyridinepentanol (yield rate: 48%). The reaction scheme is shown below.

Aufarbeitung

  1. customto react at 25° C. for 24 hours
  2. additionwere added
  3. customto react at 70° C. for 6 hours
  4. customThen, solvent was removed under reduced pressure
  5. additionthe residual material was diluted with ethyl acetate
  6. filtrationfiltered with Celite
  7. customThe material thus obtained
  8. customwas purified by column chromatography (column: silica (manufactured by Aldrich Co.), solvent: ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-edf5fc161c754e968be6808e9781b3c9
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658735B2

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