Ethyl bromoacetate → Ethyl [2-ethyl-4-(hydroxymethyl)phenoxy]acetate

HRID 1269664노트

반응식

HRID 1269664 반응식
[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][C:4]=1[OH:11])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].CCOC(C)=O>C(#N)C.O>[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][C:4]=1[O:11][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:2]

참가 물질

7

반응물 4

HCID 7748Ethyl bromoacetate2회HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 220112042-Ethyl-4-(hydroxymethyl)phenol

생성물 1

HCID 58622856Ethyl [2-ethyl-4-(hydroxymethyl)phenoxy]acetate수율 61.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

To a solution of 2-ethyl-4-(hydroxymethyl)phenol (3.67 g, 24.1 mmol) in anhydrous acetonitrile (125 mL) was added caesium carbonate (8.65 g, 26.6 mmol), the reaction mixture was then flushed with nitrogen and cooled to 0° C. before addition of ethyl bromoacetate (2.68 mL, 24.1 mmol). The reaction mixture was allowed to gradually attain room temperature and stirred for 18 h. Further ethylbromoacetate (0.26 mL, 2.4 mmol) was added and stirring continued for 4 h. The reaction mixture was diluted with water (100 mL) and then extracted EtOAc (2×100 mL). The combined organic extracts were dried (MgSO4) filtered and evaporated. Purification by Biotage™ chromatography (Silica, 90 g) eluting 4:1 cyclohexane:EtOAc, then EtOAc afforded the title compound as a pale yellow gum (3.54 g).

후처리

  1. customthe reaction mixture was then flushed with nitrogen
  2. customwas allowed to gradually attain room temperature
  3. stirringstirring
  4. waitcontinued for 4 h
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by Biotage™ chromatography (Silica, 90 g)
  9. washeluting 4:1 cyclohexane

출처 및 근거

ORD 기록
ord-4d3f48b3107a49d9a400a6667ca2203e
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199239B2

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