Diethyl Ether → 1-Bromo-6-methylundec-2-yn-5-ene

HRID 1606675ノート

反応式

HRID 1606675 の反応式
[CH3:1][C:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:3][CH2:4][C:5]#[C:6][CH2:7]O.CCOCC.P(Br)(Br)[Br:20]>N1C=CC=CC=1>[Br:20][CH2:7][C:6]#[C:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 544358746-Methylundec-2-yn-5-en-1-ol

生成物 1

HCID 540103301-Bromo-6-methylundec-2-yn-5-ene

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A mixture of 17 g. of 6-methylundec-2-yn-5-en-1-ol, 32.4 ml. of ether, and 2.07 ml. of pyridine was stirred under nitrogen in an ice-salt bath and 4.5 ml. of phosphorus tribromide was added. The ice-salt bath was then removed and the mixture was first allowed to warm to room temperature, then was heated under reflux for 2.5 hrs. The mixture was again cooled in an ice bath, and 15 ml. each of ether and water were added. The ether layer was separated, washed with aqueous sodium bicarbonate, saturated aqueous sodium chloride, dried over sodium sulfate, and evaporated. The thus obtained residue was distilled, collecting 14 g. of a mixture comprising 1-bromo-6-methylundec-2-yn-5-ene at 85°-89°C./0.005 mm.

後処理

  1. additionA mixture of 17 g
  2. customThe ice-salt bath was then removed
  3. temperaturewas heated
  4. temperatureunder reflux for 2.5 hrs
  5. temperatureThe mixture was again cooled in an ice bath
  6. additioneach of ether and water were added
  7. customThe ether layer was separated
  8. washwashed with aqueous sodium bicarbonate, saturated aqueous sodium chloride
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. distillationThe thus obtained residue was distilled
  12. customcollecting 14 g
  13. customat 85°-89°C.

出典と根拠

ORDレコード
ord-993d5f4895e74349b83ad689defa3c95
出典データセット
uspto-grants-1976_04
特許番号
US03953499

反応ノート

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