4-Penten-1-OL → 2-Pyridinepentanol

HRID 245130

反応式

HRID 245130 の反応式
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]

参加物

8

反応物 3

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

生成物 1

HCID 143474782-Pyridinepentanol収率 48%

試薬・触媒・溶媒 4

HCID 8028Tetrahydrofuran溶媒HCID 11430Potassium Carbonate溶媒HCID 21962138N,N-Dimethylformamide--water (1/1)溶媒HCID 178418397HCID 178418397、化合物溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-edf5fc161c754e968be6808e9781b3c9
出典データセット
uspto-grants-2014_02
特許番号
US08658735B2

関連ノート

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