Propargyl alcohol → 3-[4-(1h-Pyrazol-1-yl)phenyl]-2-propyn-1-ol

HRID 1166093ノート

反応式

HRID 1166093 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:13]([OH:16])[C:14]#[CH:15]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[N:8]1([C:5]2[CH:6]=[CH:7][C:2]([C:15]#[C:14][CH2:13][OH:16])=[CH:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=[N:9]1

参加物

5

反応物 2

HCID 7859Propargyl alcoholHCID 104435641-(4-bromophenyl)-1H-pyrazole

生成物 1

HCID 226309253-[4-(1h-Pyrazol-1-yl)phenyl]-2-propyn-1-ol収率 37%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒

反応条件

温度
80 °C

実験手順

A mixture of 1-(4-bromophenyl)-1H-pyrazole (prepared as described in Bull. Soc. Chim. Fr. 1966, 2832) (2.24 g, 10.04 mmol), Pd(Ph3P)2Cl2 (180 mg, 0.26 mmol), and copper(I) iodide (95 mg, 0.50 mmol) in TEA (20 mL) was stirred for 5 min, propargyl alcohol (0.70 mL, 12.02 mmol) was added, and the mixture was heated to 80° C. for 48 h. The volatiles were evaporated, ethyl acetate (50 mL) and water (50 mL) were added to the residue, and the mixture was filtered through a pad of Celite. The organic layer from the filtrate was washed with brine (50 mL), dried (Na2SO4), and concentrated. Purification by chromatography (SiO2, 3:2 hexane/ethyl acetate) yielded 0.73 g (37%) of the title compound as a brown solid. MS 199 (M+H)+.

後処理

  1. customThe volatiles were evaporated
  2. additionethyl acetate (50 mL) and water (50 mL) were added to the residue
  3. filtrationthe mixture was filtered through a pad of Celite
  4. washThe organic layer from the filtrate was washed with brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, 3:2 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-7c861f51a31c4e799360860a92b4a99d
出典データセット
uspto-grants-2003_09
特許番号
US06613747B2

反応ノート

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