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

HRID 1850410ノート

反応式

HRID 1850410 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-1135837fdf6a4678853ea470f77cd2f7
出典データセット
uspto-grants-2015_02
特許番号
US08957069B2

反応ノート

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