Methyl iodide → 4-Methoxybenzo(d)oxazole

HRID 862236

반응식

HRID 862236 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 225009354-Methoxybenzo(d)oxazole수율 91%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-a2f5f193231b487b98d619f7324fefba
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05716929

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