Hydrochloric Acid → 2-Furanyl-di-(2,4-dimethoxyphenyl)methanol

HRID 32853

반응식

HRID 32853 반응식
CO[C:3]([C:5]1[O:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[Mg]Br.[C:22](=[O:25])(O)[O-].[Na+].Cl>C1COCC1.CCOC(C)=O>[O:6]1[CH:7]=[CH:8][CH:9]=[C:5]1[C:3]([C:15]1[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][C:14]=1[O:25][CH3:22])([C:15]1[CH:14]=[CH:13][C:12]([O:11][CH3:10])=[CH:17][C:16]=1[O:18][CH3:19])[OH:4]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11902Methyl 2-furoateHCID 516892Sodium BicarbonateHCID 178491918HCID 178491918, 화합물

생성물 1

HCID 230705132-Furanyl-di-(2,4-dimethoxyphenyl)methanol

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

Methyl-2-furoate (1.58 g, 0.0125 mol) was dissolved in 100 mL of dry THF. A dropping funnel containing 50 mL of a 0.5 M solution of 2,4-dimethoxyphenylmagnesium bromide in THF (Aldrich) was attached to the reaction flask and the system was purged with argon. The reaction flask was submerged in an ice bath for 5 minutes, at which time the Grignard solution was added drop-wise over 15 minutes. After addition was complete, the reaction was allowed to warm to room temperature and was stirred overnight. A brown solution resulted after 14 hours of stirring. This solution was added to 150 g crushed ice and the slush was stirred with ˜0.5 g sodium bicarbonate during drop-wise addition of conc. HCl. A violet color was observed upon addition of acid, which was continued until effervescence was observed. The resulting neutral suspension was extracted into ˜400 mL EtOAc and the organic layer was dried over MgSO4. Removal of solvent in a rotary evaporator gave a clear/yellow oil. Upon standing in ˜30 mL EtOAc (12 h), the oil had turned deep blue and a white crystalline solid had settled out. The solid was collected and gave 1.7 g desired product. The blue solution was chromatographed in 50% EtOAc/50% hexanes and the second product to elute (deep violet upon acid treatment on TLC plate) was collected. Recrystallization of this product gave an additional 1.3 g pure desired alcohol. 3.0 g/4.6 g=65% yield.

후처리

  1. customthe system was purged with argon
  2. additionthe Grignard solution was added drop-wise over 15 minutes
  3. additionAfter addition
  4. customA brown solution resulted after 14 hours
  5. stirringof stirring
  6. additionThis solution was added to 150 g
  7. customcrushed ice
  8. additionA violet color was observed upon addition of acid, which
  9. extractionThe resulting neutral suspension was extracted into ˜400 mL EtOAc
  10. dry with materialthe organic layer was dried over MgSO4
  11. customRemoval of solvent
  12. customin a rotary evaporator
  13. customgave a clear/yellow oil
  14. customThe solid was collected

출처 및 근거

ORD 기록
ord-1534f9662f344fdf863d4d9a29a89ea7
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427679B2

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