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

HRID 2409913노트

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HRID 2409913 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5554dc387d534ff7bd6f151ecc54dd1b
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815909B2

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