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

HRID 622117

반응식

HRID 622117 반응식
[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]

참가 물질

6

반응물 3

HCID 2723783Isopropyltriphenylphosphonium iodideHCID 1247924111-BromoundecanalHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-52ad35343bd5454ca3aa594c0b1b0640
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04769386

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