p-Toluenesulfonic acid → 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran

HRID 658269

반응식

HRID 658269 반응식
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][O:9]1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 779706-Bromo-1-hexanol

생성물 1

HCID 1038602-[(6-bromohexyl)oxy]tetrahydro-2H-pyran수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 6-bromo hexan-ol (F) (2 g, 11 mmol) in CH2Cl2 (50 ml) was added dropwise dihyrdopyran (1.6 ml, 16.5 mmol) followed by para-toluenesulphonic acid (commercially available) (0.075 g). The reaction mixture was stirred at room temperature for 16 h. The dark blue solution was then washed with water (2×25 ml) then saturated hydrogen carbonate solution (25 ml) and finally with a saturated sodium chloride solution (25 ml). The organic phase was then dried (MgSO4) and the solvent was evaporated under reduced pressure. The crude material was then purified through flash silica gel chromatography (hexane/EtOAc, 10:1) to afford compound 2-(6-Bromo-hexyloxy)-tetrahydropyran (G) as an oil (0.5 g, 70%).

후처리

  1. washThe dark blue solution was then washed with water (2×25 ml)
  2. dry with materialThe organic phase was then dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude material was then purified through flash silica gel chromatography (hexane/EtOAc, 10:1)

출처 및 근거

ORD 기록
ord-15096605bc934cd5a8befa38fb27d1d7
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076426B2

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