Hydrochloric Acid → 5-(2-Furyl)-2,4-pentadienoic acid

HRID 1176104

반응식

HRID 1176104 반응식
C([Li])CCC.C(OP([CH2:14][C:15]([OH:17])=[O:16])(OCC)=O)C.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1/[CH:23]=[CH:24]/[CH:25]=O.Cl>O1CCCC1.CO.O>[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH:23]=[CH:24][CH:25]=[CH:14][C:15]([OH:17])=[O:16]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 36704(Diethoxyphosphinyl)acetic acidHCID 1549521(E)-3-(2-Furyl)acroleinHCID 178418339Butyllithium

생성물 1

HCID 39247765-(2-Furyl)-2,4-pentadienoic acid수율 69.1%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-65 °C

실험 절차

Butyllithium (70 mL of 2.5 N solution) was added to 350 mL of anhydrous tetrahydrofuran (THF) at −65° C. A solution of diethylphosphonoacetic acid (15.9 g) in 130 mL of anhydrous THF was added dropwise to the stirred solution at −65° C. over a period of 75 minutes. The resulting solution was stirred at −65° C. for an additional 30 minutes and then a solution of trans-3-(2-furyl)acrolein (10.0 g) in 85 mL of anhydrous THF was added to the reaction at −65° C. over a period of 2 hours. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was then acidified with 5% hydrochloric acid (85 mL) to a pH of 3.5 followed by addition of 30 mL of water. The aqueous layer was extracted with 50 mL of ether twice and with 50 mL of ethyl acetate once. The combined organic extract was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to give an oil. The crude oil was dissolved in 45 mL of hot methanol and then refrigerated overnight. The crystals formed were filtered and dried under vacuum to afford 9.2 g of the desired 5-(2-furyl)-2,4-pentadienoic acid. 1H NMR (acetone-d6, 300 MHz), (ppm) 7.64 (broad s, 1H), 7.42 (m, 1H), 6.86 (m, 2H), 6.58 (m, 2H), 6.05 (d, 1H).

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. extractionThe aqueous layer was extracted with 50 mL of ether twice
  4. extractionThe combined organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto give an oil
  9. customrefrigerated overnight
  10. customThe crystals formed
  11. filtrationwere filtered
  12. customdried under vacuum

출처 및 근거

ORD 기록
ord-03b4e3ac6bf04d969123cd51f8ada942
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842727B2

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