4-Benzyloxyphenylacetic acid → 2-Oxo-2-(pyridin-4-yl)ethyl 2-(4-(benzyloxy)phenyl)acetate

HRID 446793ノート

反応式

HRID 446793 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br.Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1)=[O:29]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([O:18][CH2:27][C:28](=[O:29])[C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[O:17])=[CH:13][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 810334-Benzyloxyphenylacetic acidHCID 27762394-(Bromoacetyl)pyridine hydrobromideHCID 23665647Potassium tert-butoxide2 回

生成物 1

HCID 673017532-Oxo-2-(pyridin-4-yl)ethyl 2-(4-(benzyloxy)phenyl)acetate収率 49.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a 10° C. stirred solution of 2-(4-(benzyloxy)phenyl)acetic acid (5.0 g, 0.02 mol) in MeOH (50 mL) was added a solution of potassium tert-butoxide (2.43 g, 0.02 mol) in MeOH (50 mL) under an inert atmosphere. The reaction mixture was stirred for 1 h, concentrated in vacuo and the residue was dissolved in DMF (30 mL). Potassium tert-butoxide (3.6 g, 0.03 mmol) was then added followed by 2-bromo-1-(pyridin-4-yl)ethanone hydrobromide (10.3 g, 0.05 mol), and the reaction mixture at RT. The reaction mixture was then stirred for an additional 16 h at RT, quenched with water, stirred for an additional 10 min and the precipitated solid was filtered. The crude solid was dissolved in EtOAc (200 mL) and washed with water, dried over Na2SO4, filtered and concentrated in vacuo to afford 2-oxo-2-(pyridin-4-yl)ethyl 2-(4-(benzyloxy)phenyl)acetate (3.6 g, 48%) as a solid.

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue was dissolved in DMF (30 mL)
  3. customat RT
  4. stirringThe reaction mixture was then stirred for an additional 16 h at RT
  5. customquenched with water
  6. stirringstirred for an additional 10 min
  7. filtrationthe precipitated solid was filtered
  8. dissolutionThe crude solid was dissolved in EtOAc (200 mL)
  9. washwashed with water
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ba2be6a703024eb5aa31bbd4d9aa17b6
出典データセット
uspto-grants-2013_07
特許番号
US08481534B2

反応ノート

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