Methanol → HCID 58015477、化合物

HRID 218351

反応式

HRID 218351 の反応式
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])[CH3:2].CO[CH:18](OC)[N:19]([CH3:21])[CH3:20].CO>C(OCC)(=O)C>[CH3:18][N:19]([CH3:21])/[CH:20]=[CH:2]/[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:3]

参加物

5

反応物 3

HCID 887MethanolHCID 78373Dimethylformamide dimethyl acetal2 回HCID 606426Methyl 5-acetyl-2-methoxybenzoate

生成物 1

HCID 58015477HCID 58015477、化合物収率 90.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

Methyl 5-acetyl-2-methoxybenzoate (11.98 g, 48.0 mmol) was added to N,N-dimethylformamide dimethyl acetal (44.6 g, 374.5 mmol) held under a nitrogen atmosphere. The resulting solution was heated at 95° C. for 60 minutes. Methanol (10 ml) was then removed by atmospheric distillation and further N,N-dimethylformamide dimethyl acetal (8.90 g, 74.9 mmol) added. The resulting solution was heated at 95° C. for a further 270 minutes. The reaction was then cooled to 50° C. and ethyl acetate (35 mL) added. Solvent (35 mL) is removed from the reaction by atmospheric distillation and fresh ethyl acetate (35 mL) added. Further solvent (35 mL) is removed from the reaction by atmospheric distillation and fresh ethyl acetate (50 mL) added. The reaction mixture is cooled to RT whereby the desired product crystallises out as a granular, free flowing solid. The solid was isolated by filtration, washed twice with fresh ethyl acetate (2×30 mL) and dried to constant weight to afford 11.39 g of the desired methyl 5-[(2E)-3-(dimethylamino)prop-2-enoyl]-2-methoxybenzoate (8).

後処理

  1. additionadded
  2. temperatureThe resulting solution was heated at 95° C. for a further 270 minutes
  3. temperatureThe reaction was then cooled to 50° C.
  4. customSolvent (35 mL) is removed from the reaction by atmospheric distillation and fresh ethyl acetate (35 mL)
  5. additionadded
  6. customFurther solvent (35 mL) is removed from the reaction by atmospheric distillation and fresh ethyl acetate (50 mL)
  7. additionadded
  8. temperatureThe reaction mixture is cooled to RT whereby the desired product
  9. customcrystallises out as a granular,
  10. customThe solid was isolated by filtration
  11. washwashed twice with fresh ethyl acetate (2×30 mL)
  12. customdried to constant weight

出典と根拠

ORDレコード
ord-8e86a24c94064261b40e8b03092a0b64
出典データセット
uspto-grants-2012_06
特許番号
US08198441B2

関連ノート

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