Sodium hydride → 1-[4-Benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl]ethanone

HRID 453763

反応式

HRID 453763 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH2:32][C@H:33]2[CH2:35][O:34]2)(=O)=O)=CC=1>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([O:18][CH2:32][C@H:33]2[CH2:35][O:34]2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 154187Glycidyl tosylate, (R)-HCID 3092574'-Benzyloxy-2'-hydroxyacetophenone

生成物 1

HCID 866447131-[4-Benzyloxy-2-((R)-1-oxiranylmethoxy)phenyl]ethanone収率 63.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a stirred solution of 1-(4-(benzyloxy)-2-hydroxyphenyl)ethanone (3.36 g, 13.9 mmol) in anhydrous DMF (15 ml) was added NaH (0.62 g, 15.5 mmol). The mixture was allowed to stir at RT for 30 min, and a solution of (R)-oxiran-2-ylmethyl 4-methylbenzenesulfonate (3.17 g, 13.9 mmol) in DMF was added dropwise at RT. The mixture was slowly heated to 60° C. and stirred for 3 h. The reaction was quenched by addition of water (80 ml) and extracted three times with EtOAc. The combined organic layers were extracted twice with aq 1 M NaOH and washed with water and brine. The organic layer was dried with Na2SO4 and concentrated. The crude product obtained was purified by column chromatography with EtOAc/heptane (1:1) as eluent to afford the title compound (2.64 g) as a white solid.

後処理

  1. temperatureThe mixture was slowly heated to 60° C.
  2. stirringstirred for 3 h
  3. customThe reaction was quenched by addition of water (80 ml)
  4. extractionextracted three times with EtOAc
  5. extractionThe combined organic layers were extracted twice with aq 1 M NaOH
  6. washwashed with water and brine
  7. dry with materialThe organic layer was dried with Na2SO4
  8. concentrationconcentrated
  9. customThe crude product obtained
  10. customwas purified by column chromatography with EtOAc/heptane (1:1) as eluent

出典と根拠

ORDレコード
ord-24bdc5a905cc4c6c922bb2d0f51c2bc0
出典データセット
uspto-grants-2013_07
特許番号
US08492549B2

関連ノート

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