Propargyl alcohol → 3-(5-Bromopyridin-2-yl)prop-2-yn-1-ol

HRID 2108034

반응식

HRID 2108034 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH2:9]([OH:12])[C:10]#[CH:11]>C(NCC)C.[Cu]I>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:11]#[C:10][CH2:9][OH:12])=[N:3][CH:4]=1

참가 물질

5

반응물 2

HCID 7859Propargyl alcoholHCID 693532,5-Dibromopyridine

생성물 1

HCID 139797303-(5-Bromopyridin-2-yl)prop-2-yn-1-ol수율 80.8%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8021Diethylamine용매

실험 절차

Copper (I) iodide (10 mg) was added to a solution of 2,5-dibromopyridine (4.74 g), propargyl alcohol (1.34 g) and BTPC (75 mg) in diethylamine (50 ml) and the mixture stirred overnight (18 h), under nitrogen. The solution was evaporated in vacuo and the residue treated with 8% sodium bicarbonate (50 ml) and partitioned with dichloromethane (3×50 ml). The combined extracts were dried and evaporated and the residual semi-solid purified by FCC. Eluting with ether afforded the title compound (3.43 g) as fawn crystals m.p. 121°-122°.

후처리

  1. customThe solution was evaporated in vacuo
  2. additionthe residue treated with 8% sodium bicarbonate (50 ml)
  3. custompartitioned with dichloromethane (3×50 ml)
  4. customThe combined extracts were dried
  5. customevaporated
  6. customthe residual semi-solid purified by FCC
  7. washEluting with ether

출처 및 근거

ORD 기록
ord-3b0770f191704598b3c43a06f4196909
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04937251

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