Ethylene Oxide → HCID 21464451、化合物

HRID 1940879

反応式

HRID 1940879 の反応式
[C:1]1([NH:7][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH2:21]1[O:23][CH2:22]1.O1CCOCC1>O1CCCC1>[OH:23][CH2:22][CH2:21][C:14]1[CH:13]=[N:12][CH:11]=[CH:10][C:9]=1[C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:15]

参加物

6

反応物 4

HCID 6354Ethylene OxideHCID 312751,4-DioxaneHCID 220840N-PhenylisonicotinamideHCID 178418339Butyllithium

生成物 1

HCID 21464451HCID 21464451、化合物収率 43%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-phenylisonicotinamide (1.98 g, 10 mmol) in tetrahydrofuran (40 ml) at -78° C. was added a solution of n-butyllithium (1.6M in hexanes; 13.5 ml, 21.6 mmol) and the resulting red solution stirrred for 40 minutes before addition of a solution of ethylene oxide in dioxane (3.56M; 3.0 ml, 11 mmol). After allowing the mixture to warm to room temperature over 21/2 hours, the reaction was quenched by addition of methanol (8 ml). The solvent was evaporated and the residue partitioned between ethyl acetate (70 ml) and water (25 ml). The organic layer was washed with saturated brine (25 ml), dried (MgSO4) and evaporated. The residue was chromatographed on silica eluting with 10% methanol/dichloromethane to afford the title compound as a solid (1.05 g, 43%); δH (CDCl3) 3.07 (2H, t, J 5.6 Hz, ArCH2 CH2OH), 3.70 (1H, br s, OH), 4.10 (2H, t, J 5.6 Hz, ArCH2 CH2OH), 7.15-7.19 (1H, m, ArH), 7.35-7.39 (2H, m, ArH), 7.49 (1H, d, J 5.2 Hz, ArH), 7.69-7.71 (2H, m, ArH), 8.44-8.48 (2H, m, ArH), 9.77 (1H, s, NH).

後処理

  1. customthe reaction was quenched by addition of methanol (8 ml)
  2. customThe solvent was evaporated
  3. customthe residue partitioned between ethyl acetate (70 ml) and water (25 ml)
  4. washThe organic layer was washed with saturated brine (25 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica eluting with 10% methanol/dichloromethane

出典と根拠

ORDレコード
ord-0430b92b9d694fa9a72bd1392d6bf059
出典データセット
uspto-grants-1997_12
特許番号
US05700941

関連ノート

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