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

HRID 256000

反応式

HRID 256000 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b406641224384b73a1452fc6b9686c3f
出典データセット
uspto-grants-1987_10
特許番号
US04699995

関連ノート

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