3,4-dihydro-2H-pyran → 2-(4-Bromobutoxy)tetrahydro-2H-pyran

HRID 6588

반응식

HRID 6588 반응식
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.P(Cl)(Cl)(Cl)=O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:7]1

참가 물질

6

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 1183884-Bromobutanol

생성물 1

HCID 5590192-(4-Bromobutoxy)tetrahydro-2H-pyran

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 24813Phosphorus oxychloride용매

실험 절차

To a solution of commercially available 4-bromobutan-1-ol (16) (1 equi.) and 3,4-dihydropyran (17) (1.5 equi.) in dichloromethane (3 mL/mmole), phosphorus oxychloride (0.01 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h. Then potassium carbonate (1 equi.) was added to the reaction mixture and the reaction mixture was stirred at room temperature for 1 h, quenched with water, extracted with dichloromethane, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc (ethylacetate)/hexanes) afforded 2-(4-bromobutoxy) -tetrahydropyran (18), as a colorless oil (88%).

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 1 h
  2. customquenched with water
  3. extractionextracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica gel (5% EtOAc (ethylacetate)/hexanes)

출처 및 근거

ORD 기록
ord-9c10f800168b48649bfb59f8e3d09d94
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07083832B2

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