Methyl iodide → 5-Methoxy-2-(4-methoxy-phenyl)-4-methyl-benzofuran

HRID 1836053노트

반응식

HRID 1836053 반응식
Br[C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[O:19][CH3:20].[CH2:21]([Li])CCC.CN(CCN(C)C)C.IC>C1COCC1.O>[CH3:20][O:19][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[C:2]=1[CH3:21]

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 102152694-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuranHCID 178418339Butyllithium

생성물 1

HCID 101715395-Methoxy-2-(4-methoxy-phenyl)-4-methyl-benzofuran

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

4-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuran 133 (0.282 g, 0.85 mmol) was taken into 20 mL of THF and cooled to 0° C. Then butyllithium (0.68 mL of a 2.5M solution in THF, 1.7 mmol) was added dropwise and allowed to stir for 20 minutes. Then TMEDA (0.256 mL, 1.7 mmol) was added followed by iodomethane (1.06 mL, 17 mmol). The reaction was allowed to stir overnight at room temperature. The reaction was poured into water and extracted with ethyl acetate. The combined organics was washed with water (2×), brine (1×), dried over magnesium sulfate filtered and concentrated. The resulting material was purified by column chromatography on silica gel, using a gradient of 1% to 3% ethyl acetate in hexane. The first fractions contained the product and another side product. This fraction was added to another synthesis of this compound (starting with 0.250 g 4-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuran) for the final cleavage reaction.

후처리

  1. stirringto stir overnight at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organics was washed with water (2×), brine (1×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting material was purified by column chromatography on silica gel
  8. additionThis fraction was added to another synthesis of this compound (starting with 0.250 g 4-Bromo-5-methoxy-2-(4-methoxyphenyl)-benzofuran) for the final
  9. customcleavage reaction

출처 및 근거

ORD 기록
ord-daebbd3a48624dc99c33657c35f1ed7b
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06774248B2

반응 노트

불러오는 중…