4,4-Dimethoxy-2-methylbutan-2-ol → 5-Hydroxy-2,2-dimethyl-6-propionyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one

HRID 1387601

반응식

HRID 1387601 반응식
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]([C:13](=[O:16])[CH2:14][CH3:15])=[C:8]2[C:3]=1[C:4]([CH2:18][CH2:19][CH3:20])=[CH:5][C:6](=[O:17])[O:7]2.CO[CH:23](OC)[CH2:24][C:25]([CH3:28])(O)[CH3:26]>N1C=CC=CC=1>[CH3:26][C:25]1([CH3:28])[O:1][C:2]2[C:3]3[C:4]([CH2:18][CH2:19][CH3:20])=[CH:5][C:6](=[O:17])[O:7][C:8]=3[C:9]([C:13](=[O:16])[CH2:14][CH3:15])=[C:10]([OH:12])[C:11]=2[CH:23]=[CH:24]1

참가 물질

4

반응물 2

HCID 44399804,4-Dimethoxy-2-methylbutan-2-olHCID 54948785,7-Dihydroxy-8-propionyl-4-propyl-2H-chromen-2-one

생성물 1

HCID 54948815-Hydroxy-2,2-dimethyl-6-propionyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one수율 79.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A mixture of 3 (2.60 g, 9.42 mmol) and 4,4-dimethoxy-2-methylbutan-2-ol (5.54 g, 37.7 mmol) were dissolved in anhydrous pyridine (6.5 mL). The mixture was refluxed under nitrogen for three days. After removal of the solvent in vacuo, the residue was dissolved in ethyl acetate. The ethyl acetate was washed several times with 1 N HCl and brine. It was then dried over Na2SO4. The crude product obtained by evaporation in vacuo was purified by silica gel column chromatography, eluting with 25% ethyl acetate/hexane to afford 2.55 g of 4 in 78.6% yield, mp 96-98° C. 1H-NMR (CDCl3) δ1.05 (3H, t, J=7.3 Hz, CH3); 1.22 (3H, t, J=7.5 Hz, CH3); 1.53 (6H, s, 2 CH3); 1.75 (2H, m, CH2); 2.92 (2H, t, J=7.1 Hz, CH2); 3.35 (2H, q, J=7.1 Hz, CH2); 5.56 (1H, d, J=10.0 Hz, H3); 5.98 (1H, s, H9); 6.72 (1H, d, J=10.0 Hz, H4); MS EI): 343 (5.7, M+1); 342 (22.5, M+); 327 (100, M-CH3); IR (KBr): 1728 (vs, C═O) cm−1; Anal. calcd. for C20H22O5: C, 70.16; H, 6.48; Found: C, 70.45; H, 6.92.

후처리

  1. temperatureThe mixture was refluxed under nitrogen for three days
  2. customAfter removal of the solvent in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe ethyl acetate was washed several times with 1 N HCl and brine
  5. dry with materialIt was then dried over Na2SO4
  6. customThe crude product obtained by evaporation in vacuo
  7. customwas purified by silica gel column chromatography
  8. washeluting with 25% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-ec6ff8895c67420991db477d2e566693
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06268393B1

연결된 노트

불러오는 중…