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

HRID 1166093노트

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HRID 1166093 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매

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온도
80 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-7c861f51a31c4e799360860a92b4a99d
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613747B2

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