Ammonium Chloride → Methyl 2-azido-3-(2-methoxy-3-methylphenyl)acrylate

HRID 1505656ノート

反応式

HRID 1505656 の反応式
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[C:9](OC)[CH:8]=[CH:7][C:4]=1[CH:5]=O.[N:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[N+:15]=[N-:16].CO[Na].[Cl-].[NH4+]>CO>[N:14]([C:17](=[CH:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:3]=1[O:2][CH3:1])[C:18]([O:20][CH3:21])=[O:19])=[N+:15]=[N-:16]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 2516932,4-Dimethoxy-3-methylbenzaldehydeHCID 4020482Methyl 2-azidoacetateHCID 178418582HCID 178418582、化合物

生成物 1

HCID 90405544Methyl 2-azido-3-(2-methoxy-3-methylphenyl)acrylate収率 88.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To the mixture of 2.46 g of 2-methoxy-3-methylanisaldehyde (16 mmol) and 4.72 g of methyl azidoacetate (41 mmol) in 20 mL of MeOH is added 7.6 mL of 5.4M MeONa over 30 minute at −10 degrees. After addition the mixture was stirred for additional hour at the same temperature and then transferred in cold room (4 degrees) and stirred overnight. On the morning reaction mixture was poured in 0.5 L mixture of ice and conc. ammonium chloride solution, stirred for 10 minutes and filtered off. The solid was washed with plenty of ice cold water and then moved at ambient temperature. After air drying for 1 hr the solid was dissolved in 50 mL of DCM, dried over magnesium sulfate and passed through short silica gel plug. Evaporation of solvent produced 3.5 g of methyl 2-azido-3-(2-methoxy-3-methylphenyl)acrylate, that was used in the next step without further purification.

後処理

  1. additionAfter addition the mixture
  2. customtransferred in cold room (4 degrees)
  3. stirringstirred overnight
  4. customOn the morning reaction mixture
  5. stirringstirred for 10 minutes
  6. filtrationfiltered off
  7. washThe solid was washed with plenty of ice cold water
  8. custommoved at ambient temperature
  9. customAfter air drying for 1 hr the solid
  10. dissolutionwas dissolved in 50 mL of DCM
  11. dry with materialdried over magnesium sulfate
  12. customEvaporation of solvent

出典と根拠

ORDレコード
ord-d0ee719e5025401f921542c170ec674e
出典データセット
uspto-grants-2015_12
特許番号
US09216993B2

反応ノート

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