Hydrochloric Acid → 3-(1,3-oxazol-5-yl)benzoic Acid

HRID 2409913ノート

反応式

HRID 2409913 の反応式
[C:1]([O-:4])([O-])=[O:2].[K+].[K+].[N+:7](CS(C1C=CC(C)=CC=1)(=O)=O)#[C-:8].C([C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[C:25]([O:27][CH3:28])=O)=O.Cl>CO>[O:27]1[C:25]([C:24]2[CH:29]=[C:30]([CH:31]=[CH:22][CH:23]=2)[C:1]([OH:4])=[O:2])=[CH:8][N:7]=[CH:28]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 639145Methyl 3-formylbenzoate

生成物 1

HCID 71278133-(1,3-oxazol-5-yl)benzoic Acid収率 86.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

MeOH (54 mL) was added to a round bottom flask containing K2CO3 (6.74 gm, 48.70 mmol), 1-(isocyanomethylsulfonyl)-4-methylbenzene (5.00 gm, 25.60 mmol), and methyl 3-formylbenzoate (4.00 gm, 24.37 mmol). The reaction mixture was heated at 80° C. for 3 h and then stirred at rt overnight. The mixture was concentrated under reduced pressure. The remaining residue was partitioned between EtOAc and water. The aqueous solution was isolated and acidified using 1N HCl. The acidified aqueous phase was extracted with EtOAc (2×). The organic extracts were combined, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to give the product, 3-(oxazol-5-yl)benzoic acid, (4.00 gm, 21.15 mmol, 86% yield) as a white solid. Anal. Calcd. for C10H7NO3 m/z 189.0, found: 190.1 (M+H)+. Crude product was used without purification.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe remaining residue was partitioned between EtOAc and water
  3. customThe aqueous solution was isolated
  4. extractionThe acidified aqueous phase was extracted with EtOAc (2×)
  5. washwashed with saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-5554dc387d534ff7bd6f151ecc54dd1b
出典データセット
uspto-grants-2014_08
特許番号
US08815909B2

反応ノート

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