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2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide → HCID 178447863、化合物

HRID 566164
ノート
印刷プレビュー

反応式

HRID 566164 の反応式
[Br-].[O:2]1[CH2:7][CH2:6][CH2:5][O:4][CH:3]1[CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].[CH2:35]([C@H:38]1[CH2:43][CH2:42][C@H:41]([CH:44]2[CH2:49][CH2:48][C:47](=O)[CH2:46][CH2:45]2)[CH2:40][CH2:39]1)[CH2:36][CH3:37]>C1COCC1>[CH2:35]([C@H:38]1[CH2:43][CH2:42][C@H:41]([CH:44]2[CH2:49][CH2:48][C:47](=[CH:9][CH2:8][CH:3]3[O:2][CH2:7][CH2:6][CH2:5][O:4]3)[CH2:46][CH2:45]2)[CH2:40][CH2:39]1)[CH2:36][CH3:37]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 27241682-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 178447904HCID 178447904、化合物

生成物 1

HCID 178447863HCID 178447863、化合物収率 96.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-30 °C

実験手順

A mixture of 531 g (1170 mmol) of 2-(1,3-dioxane-2-yl)ethyltriphenylphosphonium bromide and 4.0 l of THF was cooled to −30° C. under a nitrogen gas stream with a refrigeration medium. To this mixture, 121 g (1080 mmol) of t-BuOK was added, followed by stirring for 1 hour. Furthermore, 1 l of a THF solution containing 200 g (899 mmol) of 4-(trans-4-propylcyclohexyl)cyclohexanone was added dropwise to the mixture, while the temperature was maintained at −30° C. or less. After the dropping, the reaction temperature was slowly raised to room temperature, and the solution was further stirred for 5 hours. Next, the reaction solution was filtered through Celite, and the solvent was then distilled off under reduced pressure. The resulting residue was purified through silica gel column chromatography (a developing solvent: a mixed solvent of toluene/ethyl acetate=9/1 (v/v)) to obtain 277 g of crude 2-(2-(4-(trans-4-propylcyclohexyl)cyclohexylidene)ethyl)-1,3-dioxane.

後処理

  1. additionwas added dropwise to the mixture, while the temperature
  2. temperaturewas maintained at −30° C. or less
  3. temperatureAfter the dropping, the reaction temperature was slowly raised to room temperature
  4. stirringthe solution was further stirred for 5 hours
  5. filtrationNext, the reaction solution was filtered through Celite
  6. distillationthe solvent was then distilled off under reduced pressure
  7. customThe resulting residue was purified through silica gel column chromatography (a developing solvent

出典と根拠

ORDレコード
ord-737f1cddc26e4f04932710e13c1218f7
出典データセット
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06174459B1

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート