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

HRID 2108034

反応式

HRID 2108034 の反応式
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

参加物

5

反応物 2

HCID 7859Propargyl alcoholHCID 693532,5-Dibromopyridine

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8021Diethylamine溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-3b0770f191704598b3c43a06f4196909
出典データセット
uspto-grants-1990_06
特許番号
US04937251

関連ノート

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