Methyl iodide → 5-Methoxy-2-methyl-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester

HRID 2113143Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8]2[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:7]=2[O:6]1)=[O:4].[CH3:16]N(P(N(C)C)(N(C)C)=O)C.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CI>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1([CH3:16])[CH2:9][C:8]2[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:7]=2[O:6]1)=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-methoxy-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester (0.44 g, 2.0 mmol) and HMPA (0.20 mL) in THF (15 mL) at −78° C. was added LiHMDS (1M in THF, 3.0 mL, 3.0 mmol). After 15 min, methyl iodide (0.42 g, 3.0 mmol) was added and the reaction was gradually warmed to 25° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous solution of NH4Cl. The organic phase was dried and concentrated. The residue was chromatographed on silica gel eluting with 8:2 hexane:ethyl acetate to give 0.32 g 5-methoxy-2-methyl-2,3-dihydro-benzofuran-2-carboxylic acid methyl ester.

Workup

washwashed with a saturated aqueous solution of NH4Cl
customThe organic phase was dried
concentrationconcentrated
customThe residue was chromatographed on silica gel eluting with 8:2 hexane

Sources & evidence

ORD record: ord-ad064b043b9f402c9db613aba32726e9
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524882B2

Reaction notes

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