Benzyl Bromide → (E)-1-(3(benzyloxy)prop-1enyl)2-chlorobenzene

HRID 1506984노트

반응식

HRID 1506984 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH2:10][OH:11].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([O:11][CH2:10]/[CH:9]=[CH:8]/[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 11557356(2E)-3-(2-Chlorophenyl)-2-propen-1-ol

생성물 1

HCID 90033540(E)-1-(3(benzyloxy)prop-1enyl)2-chlorobenzene수율 70%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (E)-3-(2-chlorophenyl) prop-2-en-1-ol(Preparation example 1, 5.3 g, 31.6 mmole) in THF was added NaH (60% in mineral oil, 0.91 g, 37.7 mmole) and Benzyl bromide (4.12 mL, 34.8 mmole), sequently at 0° C. The reaction mixture was stirred at room temperature for 18 hr. The TLC showed complete consumption of SM. The reaction mixture was quenched with H2O at 0° C. then extracted with EtOAc. The aqueous layer was extracted with EtOAc and separated. The combined organic layer was washed with H2O, then dried over MgSO4 and evaporated under reduced pressure. The crude compound was purified by silica ge column to produce the title compound (4.94 g, 70˜90%).

후처리

  1. customsequently at 0° C
  2. customconsumption of SM
  3. customThe reaction mixture was quenched with H2O at 0° C.
  4. extractionthen extracted with EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc
  6. customseparated
  7. washThe combined organic layer was washed with H2O
  8. dry with materialdried over MgSO4
  9. customevaporated under reduced pressure
  10. customThe crude compound was purified by silica ge column

출처 및 근거

ORD 기록
ord-d3c51ccb2c9e43839281fb9c2096e137
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221783B2

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