Phosphorus tribromide → HCID 13044965, 화합물

HRID 236037노트

반응식

HRID 236037 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

HCID 13044965HCID 13044965, 화합물수율 236.2%

시약·촉매·용매 2

HCID 1049Pyridine촉매HCID 3283Diethyl Ether용매2회

반응 조건

온도
23 °C

실험 절차

A solution of phosphorus 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.

후처리

  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

출처 및 근거

ORD 기록
ord-606731b0290242a699f1cbcdc5c733e0
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04642364

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