Ethyl Bromide → (5Z)-5-Hexadecene

HRID 2211355ノート

反応式

HRID 2211355 の反応式
[Mg].[CH2:2](Br)[CH3:3].Cl[CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[Cl-].[NH4+]>O1CCCC1>[CH3:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:2][CH3:3]

参加物

6

反応物 4

HCID 6332Ethyl Bromide2 回HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 15300631HCID 15300631、化合物

生成物 1

HCID 5352234(5Z)-5-Hexadecene収率 915.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

A 1-liter reactor was charged with 5.0 g (0.206 mole) of magnesium and 90 g of tetrahydrofuran, and the reaction was initiated by adding 2 g of ethyl bromide and 46 g (0.2 mole) of 1-chloro-cis-3-tetradecene dropwise thereto under an atmosphere of nitrogen. After completion of the addition, the mixture was stirred for 2 hours under reflux of tetrahydrofuran and the resulting liquid was transferred to a 300-ml dropping funnel. Next, 30 g of tetrahydrofuran, 0.5 g of cuprous bromide and 22 g (0.204 mole) of ethyl bromide were placed in another 1-liter reactor and cooled to 0° C. Then, the above-described Grignard reagent was added dropwise thereto so that the temperature did not exceed 10° C. After completion of the reaction, 100 g of a saturated aqueous ammonium chloride solution was added and the resulting mixture was allowed to separate into two layers. The organic layer was recovered, freed of tetrahydrofuran under reduced pressure, and distilled to obtain 37.7 g of cis-5-hexadecene (purity 96%, yield 81%, b.p. 149°-152° C./3 mmHg). MS(m/e): 56(100%), 224 (M+, 21%).

後処理

  1. additionAfter completion of the addition
  2. customdid not exceed 10° C
  3. additionwas added
  4. customto separate into two layers
  5. customThe organic layer was recovered
  6. distillationdistilled

出典と根拠

ORDレコード
ord-00827a06ef0b4d01ac5364a1c4d963d3
出典データセット
uspto-grants-1995_10
特許番号
US05463149

反応ノート

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