Dimethyl Sulfate → 6-Methoxy-3-methylbenzo[d]isoxazole-7-carbaldehyde

HRID 594261노트

반응식

HRID 594261 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[C:3]=1[CH:12]=[O:13].[C:14]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:14][O:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[C:3]=1[CH:12]=[O:13]

참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 1363066756-Hydroxy-3-methylbenzo[d]isoxazole-7-carbaldehyde

생성물 1

HCID 824037016-Methoxy-3-methylbenzo[d]isoxazole-7-carbaldehyde

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
60 °C

실험 절차

A mixture of 6-hydroxy-3-methylbenzo[d]isoxazole-7-carbaldehyde (437 mg; 2.46 mmol) and K2CO3 (409 mg; 2.96 mmol) in anh. acetone (21 ml) was treated with dimethyl sulfate (373 mg; 2.96 mmol), and the resulting mixture was heated to 60° C., under nitrogen, for 1.5 h. After cooling to rt, the resulting reaction mixture was filtered, and the filtrate was concentrated to dryness under reduced pressure. DCM was added, and the mixture was washed successively with 1 M aq. NH4OH, water, and brine. The organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure to give 6-methoxy-3-methylbenzo[d]isoxazole-7-carbaldehyde as an orange solid. LC-MS (conditions A): tR=0.53 min.; [M+H]+: 192.12 g/mol.

후처리

  1. temperatureAfter cooling to rt
  2. customthe resulting reaction mixture
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated to dryness under reduced pressure
  5. additionDCM was added
  6. washthe mixture was washed successively with 1 M aq. NH4OH, water, and brine
  7. dry with materialThe organic layer was dried over anh. MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-95a078c0dae040f5a93edf9049dc5f11
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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