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

HRID 217984

反応式

HRID 217984 の反応式
[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

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 159746(-)-Benzyl (R)-glycidyl etherHCID 178461836HCID 178461836、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-66d8431238374018b9428ed53cb30a46
出典データセット
uspto-grants-2012_06
特許番号
US08198269B2

関連ノート

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