Propargyl alcohol → 3,3'-(Pyridine-2,6-diyl)di(prop-2-yn-1-ol)

HRID 1828753노트

반응식

HRID 1828753 반응식
[CH2:1]([OH:4])[C:2]#[CH:3].Br[C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[N:7]=1>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][CH2:1][C:2]#[C:3][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:3]#[C:2][CH2:1][OH:4])[N:7]=1

참가 물질

5

반응물 2

HCID 7859Propargyl alcoholHCID 122742,6-Dibromopyridine

생성물 1

HCID 220583863,3'-(Pyridine-2,6-diyl)di(prop-2-yn-1-ol)수율 134.8%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8471Triethylamine용매

실험 절차

Pd(Ph3P)4 (99 mg, 2%), CuBrSMe2 (38 mg) and propargyl alcohol (1.3 ml, 21 mmol) are added successively to a solution of 2,6-dibromopyridine (5.0 g, 21.1 mmol) in triethylamine (120 ml), and the mixture is stirred at RT for 10 min and then under reflux at 80° C. for 2 h. After cooling, the reaction mixture is filtered off through kieselguhr, and the filter cake is washed with ethyl acetate (20 ml). The organic phase is concentrated under reduced pressure. Further purification is carried out by chromatography [toluene/acetone (7:3)] on a silica gel column. This gives the title compound (2.65 g) as a colorless solid. TLC, silica gel (glass plates) [toluene/acetone (7:3)], Rf=0.15.

후처리

  1. temperatureunder reflux at 80° C. for 2 h
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered off through kieselguhr
  4. washthe filter cake is washed with ethyl acetate (20 ml)
  5. concentrationThe organic phase is concentrated under reduced pressure
  6. customFurther purification

출처 및 근거

ORD 기록
ord-fbc4ad8d0d0a466e84e6063d5e58290b
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07060716B2

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