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

HRID 1850410Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-1135837fdf6a4678853ea470f77cd2f7
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957069B2

Reaction notes

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