Tetrahydrofuran → 5-[4-(2-Hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid

HRID 1616633ノート

反応式

HRID 1616633 の反応式
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]([CH3:20])=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:12]=1.C1COCC1.[OH-].[Na+]>CCO>[OH:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]1[N:12]=[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:21])=[O:2])[O:9][C:10]=1[CH3:20]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 684911055-[4-(2-Hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

生成物 1

HCID 684930945-[4-(2-Hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Combine 5-[4-(2-hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester (2.9 g, 10.0 mmol) with THF (3 mL), EtOH (3 mL) and 2N NaOH (20 mL) and stir until hydrolysis is complete. Concentrate the mixture, dilute the residue with water and adjust the pH to 2.0-3.0 with aq HCl. Extract the mixture with EtOAc and dry the extracts over Na2SO4 before concentrating. Chromatograph the residue over silica gel (MeOH/CH2Cl2) to allow for recovery of 5-[4-(2-hydroxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid (2.14 g, 78%). MS (ES): (M+1)+ 276.2 m/z.

後処理

  1. concentrationConcentrate the mixture
  2. additiondilute the residue with water
  3. extractionExtract the mixture with EtOAc
  4. dry with materialdry the extracts over Na2SO4
  5. concentrationbefore concentrating

出典と根拠

ORDレコード
ord-0e6da45e38bb43b9ab755b4298f03c4a
出典データセット
uspto-grants-2014_07
特許番号
US08765796B2

反応ノート

読み込み中…