Phosphorus tribromide → HCID 13044965、化合物

HRID 67189ノート

反応式

HRID 67189 の反応式
P(Br)(Br)[Br:2].[CH2:5](O)[C:6]#[C:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CCOCC.N1C=CC=CC=1>[Br:2][CH2:5][C:6]#[C:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

5

反応物 2

HCID 24614Phosphorus tribromideHCID 13044963(Z,Z)-5,8-tetradecadien-2-yn-1-ol

生成物 1

HCID 13044965HCID 13044965、化合物収率 236.2%

試薬・触媒・溶媒 2

HCID 1049Pyridine触媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
23 °C

実験手順

A solution of phosphorous tribromide (0.47 g, 1.73 mmol) in absolute ether (0.5 ml) was added dropwise during five minutes to a mixture of (Z,Z)-5,8-tetradecadien-2-yn-1-ol (1.03 g, 5 mmol), and dry pyridine (14 mg, 0.18 mmol) in 8 ml of absolute ether. The reaction mixture was heated under reflux for 2.5 h, cooled to 23° C., then poured onto ice-water. It was extracted three times with ether. The combined ether extracts were washed with dilute aqueous sodium bicarbonate solution, water, dried over Na2SO4 and concentrated in vacuo. Evaporative distillation of the crude product at 145°-148° C./0.15 mm afforded 1.1 g (80.5%) of (Z,Z)-1-bromo-5,8-tetradecadien-2-yne as a pale yellow oil.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2.5 h
  3. additionpoured onto ice-water
  4. extractionIt was extracted three times with ether
  5. washThe combined ether extracts were washed with dilute aqueous sodium bicarbonate solution, water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. distillationEvaporative distillation of the crude product at 145°-148° C./0.15 mm

出典と根拠

ORDレコード
ord-101f8cc1d71b4af4a70659f11076bb26
出典データセット
uspto-grants-1982_08
特許番号
US04345084

反応ノート

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