Benzyl Bromide → [5-(Benzyloxy)pent-1-en-1-yl]benzene

HRID 1381367노트

반응식

HRID 1381367 반응식
[H-].[Na+].[C:3]1([CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[CH2:15]([O:14][CH2:13][CH2:12][CH2:11][CH:10]=[CH:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1288335-Phenyl-4-pentenol

생성물 1

HCID 53797305[5-(Benzyloxy)pent-1-en-1-yl]benzene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of sodium hydride (50%; 0.6 g) (deprived of mineral oil) in tetrahydrofuran (10 ml), there was added dropwise a solution of 5-phenyl-4-pentenol [1.66 g; known compound; cf. e.g. Journal of the Chemical Society, page 1863 (1961)] in tetrahydruforan (10 ml) in argon atmosphere at room temperature. The mixture was stirred at the same temperature for 5 minutes. A solution of benzyl bromide (1.93 g) in tetrahydrofuran (10 ml) was added dropwise and the mixture was stirred at the same temperature for 20 hours. The tetrahydrofuran was distilled off under reduced pressure and water was added to the residue, followed by extraction with ether. After washing with water and drying over magnesium sulfate, the solvent was distilled off, and the residue was subjected to silica gel chromatography, elution being carried out with chlorofrom to give 5-benzyloxy-1-phenyl-1-pentene (2.5 g) as a colorless oil.

후처리

  1. customat room temperature
  2. stirringthe mixture was stirred at the same temperature for 20 hours
  3. distillationThe tetrahydrofuran was distilled off under reduced pressure and water
  4. additionwas added to the residue
  5. extractionfollowed by extraction with ether
  6. washAfter washing with water
  7. dry with materialdrying over magnesium sulfate
  8. distillationthe solvent was distilled off
  9. washthe residue was subjected to silica gel chromatography, elution

출처 및 근거

ORD 기록
ord-e6b952aa9a6b4efbba43acc8c2c51929
출처 데이터셋
uspto-grants-1986_04
특허 번호
US04585789

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