Mandelic Acid → Daidzein

HRID 28763

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HRID 28763 반응식
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].O[CH:10]([C:14]1[CH:19]=CC=[CH:16][CH:15]=1)[C:11]([OH:13])=O.B(F)(F)F.CC[O:26][CH2:27][CH3:28].[CH3:29]S(Cl)(=O)=O>CCOCC.CCCCCC>[CH:15]1[C:14]([C:10]2[C:11](=[O:13])[C:8]3[CH:7]=[CH:6][C:4]([OH:5])=[CH:3][C:1]=3[O:2][CH:29]=2)=[CH:19][CH:28]=[C:27]([OH:26])[CH:16]=1

참가 물질

6

반응물 4

HCID 1292Mandelic AcidHCID 5054ResorcinolHCID 8000Boron trifluoride etherateHCID 31297Methanesulfonyl chloride

생성물 1

HCID 5281708Daidzein수율 44%

시약·촉매·용매 1

HCID 21584099Diethylether hexane용매2회

반응 조건

온도
70 °C

실험 절차

Resorcinol (29 mmol) and 4 hydroxyphenyl acetic acid (29 mmol) were dissolved into freshly distilled borontrifluoride etherate (20 mol eq) under nitrogen. The resulting mixture was stirred and heated at 70° C. for overnight. The reaction was monitored by TLC (80% Et2O/Hexane). The resulting mixture was cooled down at room temperature, then N,N-dimthylformamide (46.2 mL) was added dropwise. The mixture was again heated up at 50° C. for 30 minutes, then methanesulphonyl chloride (7 mL in 10 mL DMF) was added dropwise and the resulting mixture was heated at 60-70° C. until LC (80% Et2O/Hexane) shown that the reaction was almost finished, about 10 hours. After cooling down at room temperature, the mixture was poured into 400 mL ice-cold water. The precipitate was filtered. The filtrate was collected and dried. The cure product was recrystallised in 94% ethanol (aq) and gave a quite pure daidzein (3 g) in 44% yield.

후처리

  1. temperatureThe resulting mixture was cooled down at room temperature
  2. additionN,N-dimthylformamide (46.2 mL) was added dropwise
  3. temperatureThe mixture was again heated up at 50° C. for 30 minutes
  4. temperatureAfter cooling down at room temperature
  5. filtrationThe precipitate was filtered
  6. customThe filtrate was collected
  7. customdried
  8. customThe cure product was recrystallised in 94% ethanol (aq)

출처 및 근거

ORD 기록
ord-e50d098db50c4e7f9720eb7cb89fcebd
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419998B2

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