Carbon Dioxide → 3-hydroxy-4-methoxynaphtho[2,3-c]furan-1(3H)-one

HRID 1375138

반응식

HRID 1375138 반응식
CN(C)CCNC.C([Li])CCC.[CH3:13][O:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[CH:25]=[O:26].[C:27](=[O:29])=[O:28].Cl>O1CCCC1>[OH:26][CH:25]1[O:29][C:27](=[O:28])[C:17]2[CH:18]=[C:19]3[C:24](=[C:15]([O:14][CH3:13])[C:16]1=2)[CH:23]=[CH:22][CH:21]=[CH:20]3

참가 물질

7

반응물 5

HCID 280Carbon Dioxide2회HCID 313Hydrochloric AcidHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 131199931-Methoxynaphthalene-2-carbaldehydeHCID 178418339Butyllithium2회

생성물 1

HCID 210793353-hydroxy-4-methoxynaphtho[2,3-c]furan-1(3H)-one수율 3.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-20 °C

실험 절차

N,N,N′-Trimethylethylene diamine (0.82 ml, 6.3 mmol) was dissolved in tetrahydrofuran (16 ml) and cooled to −20° C. n-Butyl lithium (1.6M in hexanes, 3.9 ml, 6.24 mmol) was added and the reaction stirred at −20° C. for 15 min. 1-Methoxy-2-naphthaldehyde (0.96 g, 5.9 mmol) was added followed by n-butyl lithium (1.6M in hexanes, 11.25 ml, 18 mmol) and the reaction stirred at 25° C. for 3 h. Solid carbon dioxide was added and the reaction left until the excess carbon dioxide had sublimed. Stirring continued for 15 min before addition of hydrochloric acid (2N, 50 ml). The mixture was extracted with dichloromethane (50 ml, ×3). The combined extracts were dried (MgSO4) and the solvent evaporated under vacuum. The oily residue was preabsorbed onto silica and purified by SPE (silica, 10 g) eluting with an ethyl acetate/cyclohexane gradient to give 3-hydroxy-4-methoxynaphtho[2,3-c]furan-1 (3H)-one (50 mg, 3.7%).

후처리

  1. additionwas added
  2. stirringthe reaction stirred at 25° C. for 3 h
  3. stirringStirring
  4. extractionThe mixture was extracted with dichloromethane (50 ml, ×3)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent evaporated under vacuum
  7. customThe oily residue was preabsorbed onto silica
  8. custompurified by SPE (silica, 10 g)
  9. washeluting with an ethyl acetate/cyclohexane gradient

출처 및 근거

ORD 기록
ord-d03b82f4bcb0400b96f95b1ba5da9854
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166631B2

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