Methyl iodide → 4-Methoxybenzo(d)oxazole

HRID 502318

反応式

HRID 502318 の反応式
[OH:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:11]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[CH3:11][O:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 137206971,3-Benzoxazol-4-ol

生成物 1

HCID 225009354-Methoxybenzo(d)oxazole収率 91%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a suspension of 4-hydroxybenzoxazole (2.00 g, 14.8 mmol) (Musser et al., J. Med. Chem., 30, pp. 62-67 (1987)) in acetone (80.0 ml) was added dried K2CO3 (2.25 g, 16.3 mmol) followed by iodomethane (1.38 ml, 22.2 mmol). The reaction was heated under reflux under N2 for 4.5 h, then filtered and reduced in vacuo to afford the crude product. The resulting residue was purified by flash chromatography (25:75 ethyl acetate/hexane) to give 2.0 g (91%) of the title compound as a white crystalline solid: m.p. 72-74° C.; IR (KBr) 3089, 1619, 1610, 1503, 1496, 1322, 1275, 1090, 1071, 780, 741; 1H NMR (CDCl3) δ 8.02 (1H, s), 7.32 (1H, t, J=8.0), 7.18 (1H, d, J=8.0), 6.81 (1H, d, J=8.0), 4.04 (3H, s). Anal. Calcd. for C8H7NO2: C, 64.42; H, 4.73; N, 9.39. Found: C, 64.40; H, 4.84; N, 9.31; m/z (EI) 149 (M++1, 100%).

後処理

  1. temperatureThe reaction was heated
  2. temperatureunder reflux under N2 for 4.5 h
  3. filtrationfiltered
  4. customto afford the crude product
  5. customThe resulting residue was purified by flash chromatography (25:75 ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-51cfef438d04440a9f2a75eff0cb92ce
出典データセット
uspto-grants-2010_08
特許番号
US07772366B2

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