Methyl iodide → 1,3-Bis(ethoxymethoxy)-4-methoxy-2-methylbenzene

A solution of 4a (632 mg, 2.27 mmol) in anhydrous THF (1.94 mL) was added dropwise to a solution of nBuLi (2.5 M in hexanes, 1.48 mL, 3.70 mmol) in anhydrous THF (1.62 mL) at room temperature. After one hour, the solution was cooled to −78° C. and methyl iodide (620 μL, 9.87 mmol) was added. The resulting solution was warmed to room temperature over 12 hours, and the reaction was quenched by the addition of saturated aqueous NH4Cl. Water (5 mL) was added and the solution was extracted with CH2Cl2 (3×10 mL). Combined organic fractions were dried (Na2SO4), filtered, and concentrated. The residue was purified via column chromatography (SiO2, 8:1→5:1 Hexane:EtOAc) to afford 5a as a yellow oil (353 mg, 53%): 1H NMR (CDCl3, 500 MHz) 6.74 (d, J=9.0 Hz, 1H), 6.60 (d, J=9.0 Hz, 1H) 5.10 (s, 2H), 5.05 (s, 2H), 3.78 (q, J=7.1 Hz, 2H), 3.72 (s, 3H), 3.67 (q, J=7.1 Hz, 2H), 2.14 (s, 3H), 1.18-1.15 (m, 6H); 13C NMR (CDCl3, 125 MHz) δ 149.1, 146.5, 121.7, 109.0, 108.4, 96.2, 93.0, 64.3, 63.1, 55.1, 28.7, 14.2, 14.1, 8.8; IR (film) νmax 2918, 2359, 1487, 1260, 1248, 1082, 1055, 945, 798 cm−1; HRMS (ESI+) m/z: [M+Na]+ calcd for Cl4H22O5, 293.1365; found, 293.1357.

1. temperatureThe resulting solution was warmed to room temperature over 12 hours
2. customthe reaction was quenched by the addition of saturated aqueous NH4Cl
3. additionWater (5 mL) was added
4. extractionthe solution was extracted with CH2Cl2 (3×10 mL)
5. dry with materialCombined organic fractions were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified via column chromatography (SiO2, 8:1→5:1 Hexane:EtOAc)

ORD 기록

ord-30c251a66257448083b48b9a4420c8aa

출처 데이터셋

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08212012B2