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

HRID 594261ノート

反応式

HRID 594261 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-95a078c0dae040f5a93edf9049dc5f11
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

反応ノート

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