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

HRID 654935노트

반응식

HRID 654935 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 167845palladium(II) acetate촉매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-971fc2b89bb14941ab94843120053329
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05134128

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