3-Methoxyxanthone → HCID 14966062、化合物

HRID 1275528ノート

反応式

HRID 1275528 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13](=O)[C:14]3[C:19]([O:20][C:21]=2[CH:22]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3>CCOCC.C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C:14]3[C:19]([O:20][C:21]=2[CH:22]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3

参加物

5

反応物 2

HCID 773093-MethoxyxanthoneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 14966062HCID 14966062、化合物収率 86%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

To a suspension of lithium aluminum hydride (0.524 g, 13.8 mmole) in Et2O (30 ml) at 0° was added, dropwise, a solution of xanthone 8 (1 g, 4.42 mmole) in toluene (25 ml). The resulting mixture was stirred at room temperature for 30 min, then refluxed vigorously for 17 hrs. After cooling in an ice bath, the reaction was quenched carefully with EtOAc (1.5 ml), MeOH (1.5 ml) and finally with dilute HCl solution until the aqueous layer was acidic. The reaction mixture was partitioned between 10% EtOAc-hexanes and water. After the organic layer was separated, the aqueous layer was extracted two more times with 10% EtOAc-hexanes. The combined organic layers were washed with saturated NaCl solution, dried over anhydrous Na2SO4 and filtered through a silica gel plus. After concentration of the filtrate, 3-methoxy-9H-xanthene 9 (0.806 g, 86%) was isolated as a slightly yellow solid: m.p. 72-74° C.; 1H NMR (CDCl3): delta 7.13-7.20 (2H, m), 6.98-7.06 (3H, m), 6.58-6.62 (2H, m), 3.97 (2H, s) and 3.79 (3H, s); 1R (CHCl3): 3000, 2935, 2836, 1625, 1596, 1520, 1480, 1455, 1438, 1275, 1227, 1150, 1119, 1092, 1031, 962 and 837 cm-1.

後処理

  1. additionwas added
  2. temperaturerefluxed vigorously for 17 hrs
  3. temperatureAfter cooling in an ice bath
  4. customthe reaction was quenched carefully with EtOAc (1.5 ml), MeOH (1.5 ml) and finally with dilute HCl solution until the aqueous layer
  5. customThe reaction mixture was partitioned between 10% EtOAc-hexanes and water
  6. customAfter the organic layer was separated
  7. extractionthe aqueous layer was extracted two more times with 10% EtOAc-hexanes
  8. washThe combined organic layers were washed with saturated NaCl solution
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered through a silica gel plus

出典と根拠

ORDレコード
ord-b07dbab39984426aafe211b9a443a6c0
出典データセット
uspto-grants-2000_12
特許番号
US06162610

反応ノート

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