(2R)-2-(Phenoxymethyl)oxirane → (R)-2-Cyclohexyloxymethyl-oxirane

HRID 20380

反応式

HRID 20380 の反応式
[O:1]([CH2:8][C@H:9]1[CH2:11][O:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>O1CCCC1.[Ru]>[CH:2]1([O:1][CH2:8][C@H:9]2[CH2:11][O:10]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

参加物

5

反応物 2

HCID 1534344(2R)-2-(Phenoxymethyl)oxiraneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 29888605(R)-2-Cyclohexyloxymethyl-oxirane収率 58%

試薬・触媒・溶媒 2

HCID 23950Ruthenium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

In two separate runs, dissolve (R)-2-phenoxymethyl-oxirane (1.410 g, 9.389 mmol) in tetrahydrofuran (50 mL). Add 5% ruthenium on carbon (0.71 g) and hydrogenate at 60 psi of hydrogen gas for 40 minutes. Filter through a filtering agent, wash with tetrahydrofuran, concentrate and purify (silica gel chromatography, eluting with 5:95 to 30:70 ethyl acetate:hexanes) to give the desired compound as a clear liquid (0.850 g, 57.9% combined yield).

後処理

  1. customIn two separate runs
  2. filtrationFilter through a filtering agent
  3. washwash with tetrahydrofuran
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 5:95 to 30:70 ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-ac2d3327b15d47459b80b5ad7a66795f
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

関連ノート

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