Potassium Iodide → HCID 178444529、化合物

HRID 1849922ノート

反応式

HRID 1849922 の反応式
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH:12]=[CH:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[H-].[Na+].[I-].[K+].[CH2:21]([C@H:26]1[CH2:31][CH2:30][C@H:29]([CH2:32]Br)[CH2:28][CH2:27]1)[CH2:22][CH2:23][CH2:24][CH3:25]>C1COCC1.O>[CH2:1]([C@H:4]1[CH2:5][CH2:6][C@H:7]([CH:10]2[CH:15]=[CH:14][CH:13]([O:16][CH2:32][C@H:29]3[CH2:30][CH2:31][C@H:26]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:27][CH2:28]3)[CH2:12][CH2:11]2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 178444389HCID 178444389、化合物HCID 178447903HCID 178447903、化合物

生成物 1

HCID 178444529HCID 178444529、化合物収率 3.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under a nitrogen atmosphere, 2.4 g of 4-(trans-4-propylcyclohexyl)-2-cyclohexene-1-ol (r-1) was dissolved into 50 mL of THF, 0.52 g of 60% sodium hydride was added under ice-cooling, and the resultant mixture was stirred at room temperature for 1 hour. Thereto, 2.3 g of potassium iodide and 3.2 g of (trans-4-pentylcyclohexyl)bromomethane (r-2) dissolved in 30 mL of THF were added, and the resultant mixture was stirred under heating reflux for 8 hours. The resultant reaction mixture was poured into water, and subjected to extraction with toluene. Combined organic layers were washed with saturated brine, and then dried over anhydrous magnesium sulfate. A solvent was evaporated under reduced pressure, and a residue was purified by silica gel column chromatography (eluate:heptane:toluene=1:1 (in a volume ratio)), and further purified by recrystallization from a mixed solvent of heptane:Solmix A-11 (registered tradename; Japan Alcohol Trading Co., Ltd.)=1:2 (in a volume ratio), and thus 0.15 g of 6-(trans-4-propylcyclohexyl)-3-(trans-4-pentylcyclohexyl)methoxy cyclohexene [compound (1-3-1-18) was obtained.

後処理

  1. additionwas added under ice-
  2. temperaturecooling
  3. additionwere added
  4. temperatureunder heating
  5. temperaturereflux for 8 hours
  6. customThe resultant reaction mixture
  7. extractionsubjected to extraction with toluene
  8. washCombined organic layers were washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customA solvent was evaporated under reduced pressure
  11. customa residue was purified by silica gel column chromatography (eluate:heptane
  12. customtoluene=1:1 (in a volume ratio)), and further purified by recrystallization from a mixed solvent of heptane

出典と根拠

ORDレコード
ord-3ed26e9f75214a168627206fa4673557
出典データセット
uspto-grants-2015_02
特許番号
US08956552B2

反応ノート

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