Sodium hydride → HCID 86644716、化合物

HRID 2365976ノート

反応式

HRID 2365976 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:18])=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=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:10]=[CH:11][C:12]([O:18][CH2:32][C@H:33]2[CH2:35][O:34]2)=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=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 128709281-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one

生成物 1

HCID 86644716HCID 86644716、化合物収率 63.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a stirred solution of 1-(5-benzyloxy-2-hydroxyphenyl)ethanone (3.0 g, 12.4 mmol) in anhydrous DMF (15 ml) was added NaH (0.55 g, 13.6 mmol). The mixture was allowed to stir at RT for 30 min and then heated to 60° C. A solution of (R)-oxiran-2-ylmethyl 4-methylbenzenesulfonate (2.83 g, 12.4 mmol) in DMF was added dropwise at 60° C. during 1 h. Stirring was then continued at 60° C. for 3 h. The cooled 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/toluene as eluent to afford the title compound (2.35 g) as a white solid.

後処理

  1. temperatureheated to 60° C
  2. stirringStirring
  3. waitwas then continued at 60° C. for 3 h
  4. customThe cooled reaction
  5. customwas quenched by addition of water (80 ml)
  6. extractionextracted three times with EtOAc
  7. extractionThe combined organic layers were extracted twice with aq 1 M NaOH
  8. washwashed with water and brine
  9. dry with materialThe organic layer was dried with Na2SO4
  10. concentrationconcentrated
  11. customThe crude product obtained
  12. customwas purified by column chromatography with EtOAc/toluene as eluent

出典と根拠

ORDレコード
ord-bd3ec28b228245e29a92fe640136a5ac
出典データセット
uspto-grants-2014_04
特許番号
US08697723B2

反応ノート

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