Methanol → 2-Phenyl-5-(propan-2-yl)-1,3-oxazole-4-carboxylic acid

HRID 2236171ノート

反応式

HRID 2236171 の反応式
C([O:8][C:9]([C:11]1[N:12]=[C:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:14][C:15]=1[CH:16]([CH3:18])[CH3:17])=[O:10])C1C=CC=CC=1.O1CCCC1.CO.[H-].[OH-].[Li+]>O>[CH:16]([C:15]1[O:14][C:13]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[N:12][C:11]=1[C:9]([OH:10])=[O:8])([CH3:18])[CH3:17]

参加物

6

反応物 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 44556966HCID 44556966、化合物HCID 86597229HCID 86597229、化合物

生成物 1

HCID 201167172-Phenyl-5-(propan-2-yl)-1,3-oxazole-4-carboxylic acid収率 41.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Solution of 5-isopropyl-2-phenyl-oxazole-4-carboxylic acid benzyl ester (830 mg, 2.59 mmol) in a mix of tetrahydrofuran, methanol and water (3:1:1, 10 mL) was treated with lithium hydroxide monohydride (258 mg, 6.5 mmol) at room temperature for an hour. After the reaction was complete, solvent was removed. To the residue, water and dichloromethane were added, and white precipitate formed. After filtering off the solid, filtrate was collected and the phases were separated. The pH of the aqueous layer was adjusted to 1˜2 with dilute hydrochloride acid (1N). Then the aqueous layer was extracted with ethyl acetate three times. The ethyl acetate layers were collected, dried over sodium sulfate, and concentrated in vacuo. Flash chromatography (Merck silica gel 60, 230-400 mesh, 0-80% ethyl acetate in hexane for 20 min) gave 5-isopropyl-2-phenyl-oxazole-4-carboxylic acid (247 mg, 41%) as a white solid. LCMS calcd for C13H13NO3 (m/e) 231, obsd 232 (M+H).

後処理

  1. customsolvent was removed
  2. additionTo the residue, water and dichloromethane were added
  3. customwhite precipitate formed
  4. filtrationAfter filtering off the solid, filtrate
  5. customwas collected
  6. customthe phases were separated
  7. extractionThen the aqueous layer was extracted with ethyl acetate three times
  8. customThe ethyl acetate layers were collected
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2b3026a5ae6e4857b4fa8fc9f5a0e313
出典データセット
uspto-grants-2010_05
特許番号
US07714126B2

反応ノート

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