Propargyl alcohol → HCID 11401073、化合物

HRID 1061592ノート

反応式

HRID 1061592 の反応式
[CH2:1]([OH:4])[C:2]#[CH:3].Br[C:6]1[O:7][C:8](Br)=[CH:9][CH:10]=1>C(N)CC.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.[Cu]I>[OH:4][CH2:1][C:2]#[C:3][C:6]1[O:7][C:8]([C:3]#[C:2][CH2:1][OH:4])=[CH:9][CH:10]=1

参加物

6

反応物 2

HCID 7859Propargyl alcohol2 回HCID 108788462,5-dibromofuran

生成物 1

HCID 11401073HCID 11401073、化合物収率 95.4%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 7852Propylamine溶媒

実験手順

Pd(Ph3P)4 (580 mg, 3%), CuI (140 mg, 2%) and propargyl alcohol (4.65 ml, 67.7 mmol) are added successively to a solution of 2,5-dibromofuran (5.1 g, 22.6 mmol) in n-propylamine (100 ml), and the mixture is stirred at RT for 1 h and then under reflux for 24 h. More propargyl alcohol (2.0 ml, 33 mmol) is then added and the mixture is stirred under reflux for another 8 h. After cooling, the reaction mixture is filtered off with suction through kieselguhr and washed with ethyl acetate (50 ml). The organic phase is concentrated under reduced pressure. Further purification is carried out by chromatography [Tol/Ac (8:2)] over a silica gel column. This gives the title compound (3.8 g) as a colorless solid. TLC, silica gel (glass plates), [toluene/acetone (8:2)], Rf=0.40.

後処理

  1. temperatureunder reflux for 24 h
  2. stirringthe mixture is stirred
  3. temperatureunder reflux for another 8 h
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture is filtered off with suction through kieselguhr
  6. washwashed with ethyl acetate (50 ml)
  7. concentrationThe organic phase is concentrated under reduced pressure
  8. customFurther purification

出典と根拠

ORDレコード
ord-539cd9c952d342438041f66c6603683b
出典データセット
uspto-grants-2005_11
特許番号
US06960588B1

反応ノート

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