Diethyl Ether → 2-(7-Hydroxy-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one

HRID 33809

反応式

HRID 33809 の反応式
N[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[S:12][C:11]1[C:10]([C:16]3[O:17][C:18]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:19][C:20](=[O:22])[CH:21]=3)=[CH:9][CH:8]=[CH:7][C:6]=1[S:5]2.F[B-](F)(F)F.[H+].N(OCCCC)=[O:36].C(OCC)C>C(O)C.O>[OH:36][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[S:12][C:11]1[C:10]([C:16]3[O:17][C:18]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[CH:19][C:20](=[O:22])[CH:21]=3)=[CH:9][CH:8]=[CH:7][C:6]=1[S:5]2

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 10996Butyl nitriteHCID 28118Tetrafluoroboric acidHCID 597974272-(7-Amino-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one

生成物 1

HCID 597974292-(7-Hydroxy-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one収率 100.7%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a solution of 2-(7-Amino-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one (21) (575 mg, 1.4 mmol) was suspended in ethanol (5 mL) was added tetrafluoroboric acid (54 wt % in ether, 3 ml, 1.68 mmol). The mixture was stirred at room temperature for 10 minutes before being cooled to 0° C. Butyl nitrite (220 μl, 2.8 mmol) was then added dropwise and the mixture stirred for 30 minutes before the addition of diethyl ether (40 ml) which caused a precipitate to form. The solid was collected by filtration and washed with cold diethylether (30 ml) then added to a solution of cupric nitrate trihidrate (210 g, 870 mmol) and cuprous oxide (190 mg, 1.31 mmol) in water (300 ml). The reaction was stirred for 12 hours and then filtered. The filtrant was washed with water, dried in a desiccator and used without further purification give the title compound (0.58 g, 100%). NMR (300 MHz, CDCl3): δH=10.08 (1H, bs); 7.76 (1H, dd); 7.60 (1H, dd); 7.46 (1H, dd); 7.35 (1H, dd); 7.02 (1H, d); 6.74 (1H, dd); 6.24 (1H, d); 5.55 (1H, d); 3.69 (H, m), 3.36 (4H, m); m/z (LC-MS, ESP), RT=3.83 min, (M++1)=412

後処理

  1. temperaturebefore being cooled to 0° C
  2. customto form
  3. filtrationThe solid was collected by filtration
  4. washwashed with cold diethylether (30 ml)
  5. stirringThe reaction was stirred for 12 hours
  6. filtrationfiltered
  7. washThe filtrant was washed with water
  8. customdried in a desiccator
  9. customused without further purification

出典と根拠

ORDレコード
ord-b92d9026764d4d1fb0183695bfbe077d
出典データセット
uspto-grants-2008_09
特許番号
US07429660B2

関連ノート

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