Ethyl Bromide → (5Z)-5-Hexadecene

HRID 861707노트

반응식

HRID 861707 반응식
[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]

참가 물질

6

반응물 4

HCID 6332Ethyl Bromide2회HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 15300631HCID 15300631, 화합물

생성물 1

HCID 5352234(5Z)-5-Hexadecene수율 915.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-fac0a27091a348d5be65e0c47cf22182
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05714649

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