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 362223

反応式

HRID 362223 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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 1N 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) δ 1.05 (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.

後処理

  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 1N 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

出典と根拠

ORDレコード
ord-4fbb9a938f2146f2b8731d6a713ee26b
出典データセット
uspto-grants-1999_02
特許番号
US05869324

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