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

HRID 1828753ノート

反応式

HRID 1828753 の反応式
[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

参加物

5

反応物 2

HCID 7859Propargyl alcoholHCID 122742,6-Dibromopyridine

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fbc4ad8d0d0a466e84e6063d5e58290b
出典データセット
uspto-grants-2006_06
特許番号
US07060716B2

反応ノート

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