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

HRID 1269664ノート

反応式

HRID 1269664 の反応式
[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]

参加物

7

反応物 4

HCID 7748Ethyl bromoacetate2 回HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 220112042-Ethyl-4-(hydroxymethyl)phenol

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4d3f48b3107a49d9a400a6667ca2203e
出典データセット
uspto-grants-2007_04
特許番号
US07199239B2

反応ノート

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