(R)-2-Benzhydryloxirane → (2S)-1,1-diphenyl-pent-4-ene-2-ol

HRID 78918ノート

反応式

HRID 78918 の反応式
[CH:1]([C@@H:14]1[CH2:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]([Mg]Br)=[CH2:18]>C1COCC1.[Cu]I>[C:2]1([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:14]([OH:15])[CH2:16][CH:17]=[CH2:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 11789056(R)-2-Benzhydryloxirane2 回HCID 178418507HCID 178418507、化合物

生成物 1

HCID 11390776(2S)-1,1-diphenyl-pent-4-ene-2-ol収率 70.5%

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2 回

実験手順

(2R)-2-benzhydryl-oxirane (0.5 g, 2.38 mmol) 23a was dissolved in dry THF (5 ml) and was added into a dry THF solution at −78° C. containing CuI (0.045 g, 0.24 mmol) and vinylmagnesium bromide (5.95 ml of 1.0M solution in THF, 5.95 mmol). The reaction mixture was stirred and allowed to reach room temperature over a period of 2 h, and then quenched with saturated NH4Cl solution. The aqueous phase was extracted with ethyl acetate (3×30 ml). The combined organic phase was washed with brine and dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by flash chromatography on silica gel (Hexane/Ethyl Ether=4:1) to give 0.4 g (2S)-1,1-diphenyl-pent-4-ene-2-ol (70%, [α]D=(−)25, c=1, MeOH).

後処理

  1. customquenched with saturated NH4Cl solution
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×30 ml)
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed
  6. customthe residue was purified by flash chromatography on silica gel (Hexane/Ethyl Ether=4:1)

出典と根拠

ORDレコード
ord-dbe55d24509644e7b0f7b0f1ae8f8c6f
出典データセット
uspto-grants-2014_09
特許番号
US08841464B2

反応ノート

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