1,1-Dibromoethane → 4-(2-(Tetrahydropyran-2-yloxy)ethyl)phenethyl alcohol

HRID 440468노트

반응식

HRID 440468 반응식
[Mg].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1.BrC(Br)C.[CH2:22]1[O:24][CH2:23]1.O1CCCC1>O1CCCC1.O>[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:22][CH2:23][OH:24])=[CH:13][CH:12]=1

참가 물질

7

반응물 4

HCID 112011,1-DibromoethaneHCID 5462224MagnesiumHCID 133067582-(4-bromophenethoxy)tetrahydro-2H-pyranHCID 21868110Ethylene oxide tetrahydrofuran

생성물 1

HCID 542369074-(2-(Tetrahydropyran-2-yloxy)ethyl)phenethyl alcohol수율 48.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Magnesium (1.31 g, 53.90 mmol) was added to a solution of 4-(2-(tetrahydropyran-2-yloxy)ethyl)bromobenzene (14.00 g, 49.09 mmol) in tetrahydrofuran (20 ml). Then dibromoethane (0.1 ml) was added under an atmosphere of nitrogen gas, and the mixture was stirred under room temperature for 1 hour. After cooling to ice-cooling temperature, 2M-ethylene oxide/tetrahydrofuran solution (49.09 ml, 98.18 mmol) was added, and the mixture was stirred at room temperature for 2 hours. Then, water (40 ml) was added to the reaction mixture. The mixture was extracted with ethyl ether and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=8/2) to give the desired 4-(2-(tetrahydropyran-2-yloxy)ethyl)phenethyl alcohol (6.00 g, 42%) .

후처리

  1. temperatureAfter cooling to ice-
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. extractionThe mixture was extracted with ethyl ether
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=8/2)

출처 및 근거

ORD 기록
ord-c27c171ee7d3431da8a285456059b5a1
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05519139

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