Methyl iodide → HCID 68674503, compound

HRID 1446381Notes

Reaction equation

HRID 1446381 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[C:10]([O:12][CH3:13])=[O:11].CI.[CH3:16]C(C)([O-])C.[K+]>O1CCCC1.C(OCC)(=O)C>[CH3:16][C:2]1([C:10]([O:12][CH3:13])=[O:11])[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 12836151HCID 12836151, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 68674503HCID 68674503, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2,3-dihydrobenzofuran-2-carboxylate (Step A, 1.0 g, 5.5 mmol) and methyl iodide (1.8 mL, 28 mmol) in 20 mL of anhydrous tetrahydrofuran at −78° C. was added potassium tert-butoxide (1 M in tetrahydrofuran, 8.4 mL, 8.4 mmol). The reaction was allowed to warm to room temperature overnight, and the resulting mixture was diluted with ethyl acetate (100 mL), washed with aqueous saturated ammonium chloride (100 mL) and water, dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The residue was purified by flash column chromatography eluted with 2-5% ethyl acetate in hexane to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.16 (d, 1H), 7.12 (t, 1H), 6.86 (t, 1H), 6.76 (d, 1H), 3.75 (s, 3H), 3.58 (d, 1H), 3.17 (d, 1H), 1.66 (s, 3H).

Workup

  1. washwashed with aqueous saturated ammonium chloride (100 mL) and water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by flash column chromatography
  6. washeluted with 2-5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9aec2cb3a18c4be1b1f5327a4f001ec1
Source dataset
uspto-grants-2010_02
Patent number
US07667053B2

Reaction notes

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