Methyl iodide → 2-(Methoxymethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran

HRID 1850410노트

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HRID 1850410 반응식
[H-].[Na+].[CH3:3][C:4]1([CH2:16][OH:17])[CH2:8][C:7]2[C:9]([CH3:15])=[CH:10][C:11]([CH3:14])=[C:12]([CH3:13])[C:6]=2[O:5]1.[CH3:18]I.[Cl-].[NH4+]>C(OCC)(=O)C.C1COCC1>[CH3:18][O:17][CH2:16][C:4]1([CH3:3])[CH2:8][C:7]2[C:9]([CH3:15])=[CH:10][C:11]([CH3:14])=[C:12]([CH3:13])[C:6]=2[O:5]1

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11998626(2,4,6,7-Tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanol

생성물 1

HCID 667591922-(Methoxymethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran수율 66%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

60% sodium hydride (60 mg, 1.46 mmol) was added to a solution of THF (3 mL) containing (2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methanol (200 mg, 0.970 mmol) synthesized in Reference Example 122 under ice-cooling condition, and the mixture was stirred at 0° C. for 20 minutes. After that, methyl iodide (413 mg, 2.19 mmol) was added thereto, and the mixture was warmed to room temperature, followed by stirring for 15 hours. The reaction solution was poured into a saturated ammonium chloride aqueous solution, and extraction was performed using ethyl acetate. The extract was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 98:2-92:8) to give 140 mg of the title compound (yield: 66%).

후처리

  1. customsynthesized in Reference Example 122 under ice-
  2. temperaturecooling condition
  3. temperaturethe mixture was warmed to room temperature
  4. stirringby stirring for 15 hours
  5. washThe extract was washed with saturated saline
  6. customdried
  7. concentrationfollowed by concentration under reduced pressure
  8. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 98:2-92:8)

출처 및 근거

ORD 기록
ord-1135837fdf6a4678853ea470f77cd2f7
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957069B2

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