2-Bromopyridine → 5-(Pyridin-2-yl)pent-4-yn-1-ol

HRID 654935ノート

反応式

HRID 654935 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:27]([OH:32])[CH2:28][CH2:29][C:30]#[CH:31].[OH-].[Na+]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:31]#[C:30][CH2:29][CH2:28][CH2:27][OH:32]

参加物

8

反応物 4

HCID 79732-BromopyridineHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 793464-Pentyn-1-ol

生成物 1

HCID 109973535-(Pyridin-2-yl)pent-4-yn-1-ol

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 167845palladium(II) acetate触媒HCID 8471Triethylamine溶媒

実験手順

A mixture of 2-bromopyridine (5 g, 31.6 mmol), palladium (II) acetate (5 mg), copper (I) iodide (5 mg), triphenylphosphine (5 mg) in triethylamine (40 ml) was deaerated with argon for 5 minutes. After 4-pentyn-1-ol (3.49 ml, 37.9 mmol) was added, the solution was rapidly heated to reflux under argon and conditions maintained for 22 hours. On cooling, the mixture was poured into 2M sodium hydroxide (ca. 30 ml) and extracted thoroughly with ethyl acetate. Evaporation of the dried (magnesium sulphate) extracts gave an oil, which was flash chromatographed on silica using 60% ethyl acetate/chloroform. Fractions with Rf of about 0.12 on evaporation gave the title alcohol as a pale brown oil.

後処理

  1. temperaturethe solution was rapidly heated
  2. temperatureto reflux under argon
  3. temperatureconditions maintained for 22 hours
  4. temperatureOn cooling
  5. extractionextracted thoroughly with ethyl acetate
  6. customEvaporation of the
  7. dry with materialdried (magnesium sulphate)
  8. customextracts gave an oil, which
  9. customchromatographed on silica using 60% ethyl acetate/chloroform
  10. customFractions with Rf of about 0.12 on evaporation

出典と根拠

ORDレコード
ord-971fc2b89bb14941ab94843120053329
出典データセット
uspto-grants-1992_07
特許番号
US05134128

反応ノート

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