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

HRID 548972노트

반응식

HRID 548972 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 mL) 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 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of solvent under vacuo

출처 및 근거

ORD 기록
ord-83adb961d2c94029b64a60c60b3c9230
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943634B2

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