4-Penten-1-OL → 2-Pyridinepentanol

HRID 245130

Reaction equation

HRID 245130 reaction equation
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]

Participants

8

Reactant 3

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

Product 1

HCID 143474782-PyridinepentanolYield 48%

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolventHCID 11430Potassium CarbonateSolventHCID 21962138N,N-Dimethylformamide--water (1/1)SolventHCID 178418397HCID 178418397, compoundSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-edf5fc161c754e968be6808e9781b3c9
Source dataset
uspto-grants-2014_02
Patent number
US08658735B2

Linked notes

Loading…