Diethyl Ether → (2R)-1-(benzyloxy)pent-4-en-2-ol

HRID 217984

반응식

HRID 217984 반응식
[CH3:1][CH2:2]OCC.[CH2:6]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C@@H:7]1[O:9][CH2:8]1.C([Mg]Cl)=C.[Cl-].[NH4+]>C1COCC1.[Cu]I>[CH2:11]([O:10][CH2:6][C@H:7]([OH:9])[CH2:8][CH:1]=[CH2:2])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 159746(-)-Benzyl (R)-glycidyl etherHCID 178461836HCID 178461836, 화합물

생성물 1

HCID 10375318(2R)-1-(benzyloxy)pent-4-en-2-ol

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

Ether (100 ml) and copper(I) iodide (580 mg) were added to a solution of (R)-benzyl glycidyl ether (10.0 g) in THF (100 ml). The mixture was cooled to −78° C., and vinylmagnesium chloride (1.38 M, 53.0 ml) was added dropwise. The mixture was stirred overnight with gradual heating to room temperature. Ice was added to the reaction solution, and an ammonium chloride solution was further added. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with an ammonium chloride solution. The insoluble matter was removed by filtration through celite, and the solvent was evaporated under reduced pressure to obtain the title compound (12.5 g).

후처리

  1. temperaturewith gradual heating to room temperature
  2. additionIce was added to the reaction solution
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe organic layer was washed with an ammonium chloride solution
  5. customThe insoluble matter was removed by filtration through celite
  6. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-66d8431238374018b9428ed53cb30a46
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198269B2

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