Iodine → 1-(3-(Benzyloxy)phenyl)cyclopentanol

HRID 501796

반응식

HRID 501796 반응식
[Mg].II.[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](Br)[CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:19]1(=[O:24])[CH2:23][CH2:22][CH2:21][CH2:20]1.[Cl-].N>C(OCC)C>[CH2:4]([O:11][C:12]1[CH:13]=[C:14]([C:19]2([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:15]=[CH:16][CH:17]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

7

반응물 5

HCID 807IodineHCID 8452CyclopentanoneHCID 27566381-(Benzyloxy)-3-bromobenzeneHCID 5462224MagnesiumHCID 20976574Ammonia chloride

생성물 1

HCID 230215691-(3-(Benzyloxy)phenyl)cyclopentanol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

실험 절차

1.85 g of magnesium was suspended in 15 mL of diethyl ether, to which a catalytic amount of iodine was added and then a solution of 20.00 g of 1-(benzyloxy)-3-bromobenzene in 40 mL of diethyl ether was added dropwise and this mixture was stirred for 8 hours while heating it under reflux. The reaction mixture was cooled to 5° C., to which a solution of 6.72 mL of cyclopentanone in 20 mL of diethyl ether was added dropwise, and this mixture was stirred for one hour at room temperature. Then an aqueous solution of ammonia chloride was added to the ice-cooled reaction mixture, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=10:1] to yield 7.65 g of 1-[3-(benzyloxy)phenyl] cyclopentanol as yellow oil.

후처리

  1. additionwas added
  2. temperaturewhile heating it
  3. temperatureunder reflux
  4. additionwas added dropwise
  5. stirringthis mixture was stirred for one hour at room temperature
  6. temperaturecooled
  7. customreaction mixture
  8. customthe organic phase was separated
  9. washAfter the resultant organic phase was washed with water
  10. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled out under reduced pressure
  12. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=10:1]

출처 및 근거

ORD 기록
ord-19059c6449ff4f93ae4008210309f040
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772285B2

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