1-Iodohexane → 1-Methoxy-3-(1-octynyl)benzene

HRID 256000

반응식

HRID 256000 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]#[CH:10])[CH:6]=[CH:7][CH:8]=1.C([Li])CCC.I[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>O1CCCC1.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:6]=[CH:7][CH:8]=1

참가 물질

6

반응물 3

HCID 125271-IodohexaneHCID 6407531-Ethynyl-3-methoxybenzeneHCID 178418339Butyllithium

생성물 1

HCID 112644061-Methoxy-3-(1-octynyl)benzene

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-70 °C

실험 절차

3-Methoxyphenylacetylene [5.00 g, 0.032M, prepared by the method of E. Negishi et al, J. Org. Chem. 45 2526-8, (1980)] was dissolved in dry tetrahydrofuran (15 ml), cooled to -70° C. under nitrogen, and n-butyl lithium, 1.6M in hexane, (24.40 ml, 0.038M), added dropwise. After stirring for 0.5 h, iodohexane (8.00 g, 0.038M), dissolved in dry tetrahydrofuran, (15 ml) was added dropwise. The rection was warmed slowly to room temperature, refluxed overnight, then cooled. The solution was then quenched with water, acidified with dilute hydrochloric acid and extracted with diethyl ether (twice). The organic phases were combined, washed with water and dried, (MgSO4). Evaporation in vacuo affored 7.71 g of product as an orange oil.

후처리

  1. additionwas added dropwise
  2. temperatureThe rection was warmed slowly to room temperature
  3. temperaturerefluxed overnight
  4. temperaturecooled
  5. customThe solution was then quenched with water
  6. extractionextracted with diethyl ether (twice)
  7. washwashed with water
  8. customdried
  9. customEvaporation in vacuo affored 7.71 g of product as an orange oil

출처 및 근거

ORD 기록
ord-b406641224384b73a1452fc6b9686c3f
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04699995

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