Isopropyltriphenylphosphonium iodide → 1-Bromo-12-methyl-11-tridecene

HRID 622117

反応式

HRID 622117 の反応式
[I-].[CH:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:4])[CH3:3].C([Li])CCC.[Br:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=O>O1CCCC1.CCCCCC>[Br:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[C:2]([CH3:4])[CH3:3]

参加物

6

反応物 3

HCID 2723783Isopropyltriphenylphosphonium iodideHCID 1247924111-BromoundecanalHCID 178418339Butyllithium

生成物 1

HCID 212937251-Bromo-12-methyl-11-tridecene

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-40 °C

実験手順

Isopropyltriphenylphosphonium iodide (6 g, 14 mmoles) was suspended in tetrahydrofuran (120 ml), stirred at -40° C. and treated with n-butyllithium (14 mmoles) dissolved in hexane (2.5M). The mixture was stirred at -40° C. for 15 minutes, cooled to -75° C. and treated with a solution of 1-bromo-11-oxoundecane (2.8 g, 11.5 mmoles) in tetrahydrofuran (30 ml). The mixture was stirred at -75° C. for 15 minutes, allowed to warm to 25° C. and concentrated in vacuo. The residue was triturated with hexane, filtered and the filtrate concentrated in vacuo. The residue was chromatographed on silica gel eluted with hexane to afford 1-bromo-12-methyl-11-tridecene.

後処理

  1. stirringThe mixture was stirred at -40° C. for 15 minutes
  2. temperaturecooled to -75° C.
  3. stirringThe mixture was stirred at -75° C. for 15 minutes
  4. temperatureto warm to 25° C.
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with hexane
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customThe residue was chromatographed on silica gel
  10. washeluted with hexane

出典と根拠

ORDレコード
ord-52ad35343bd5454ca3aa594c0b1b0640
出典データセット
uspto-grants-1988_09
特許番号
US04769386

関連ノート

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