Hydrochloric Acid → (Z)-3-(7-methoxy-4-methyloxycarbonylbenzo[b]furan-2-yl)-2-propenoic acid

HRID 1091835노트

반응식

HRID 1091835 반응식
[CH3:1][O:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]([CH:14]=O)[O:10][C:9]=2[C:8]([O:16][CH3:17])=[CH:7][CH:6]=1)=[O:4].C(O)(=O)[CH2:19][C:20]([OH:22])=[O:21].N1CCCCC1.Cl>C1(C)C=CC=CC=1>[CH3:17][O:16][C:8]1[C:9]2[O:10][C:11](/[CH:14]=[CH:19]\[C:20]([OH:22])=[O:21])=[CH:12][C:13]=2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 86636828Methyl-2-formyl-7-methoxybenzo[b]furan-4-carboxylate

생성물 1

HCID 66592575(Z)-3-(7-methoxy-4-methyloxycarbonylbenzo[b]furan-2-yl)-2-propenoic acid수율 76.4%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a well stirred solution of Methyl-2-formyl-7-methoxybenzo[b]furan-4-carboxylate (from step 7) (2.0 g, 8.53 mmol) in toluene (50.0 mL) was added malonic acid (1.33 g, 12.80 mmol) and Piperidine (0.5 ml). The reaction mixture was then refluxed for 3-4 hours. Reaction mixture was cooled to room temperature, acidified with 10% aqueous HCl solution and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with water (2×100 mL0 and dried over anhydrous sodium sulfate. Removal of solvent under vacuo gave product (1.8 g) as light yellow solid.

후처리

  1. temperatureThe reaction mixture was then refluxed for 3-4 hours
  2. customReaction mixture
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. washThe combined organic layers were washed with water (2×100 mL0
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of solvent under vacuo

출처 및 근거

ORD 기록
ord-285f6e1d9fdc44d296e8c958c1814831
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129401B2

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