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

HRID 453763

반응식

HRID 453763 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-24bdc5a905cc4c6c922bb2d0f51c2bc0
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492549B2

연결된 노트

불러오는 중…