Реакция #503448

Уравнение реакции

t-BuLi

pentane

6-nitroveratraldehyde

5-iodo-1,2,3-trimethoxybenzene

→

title compound 241

Выход 40.2%

(4,5-Dimethoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol

Выход 40.2%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe resulting mixture was stirred for 2 h
3. 3
   Температураslowly warmed up to 0° C.
4. 4
   Другоеquenched with saturated aqueous solution of NH4Cl
5. 5
   Температураto warm-up to rt
6. 6
   ДругоеSolvent was removed in vacuo
7. 7
   Другоеthe residue was partitioned between water and DCM
8. 8
   ДругоеOrganic layer was collected
9. 9
   Промывкаwashed with brine
10. 10
    Сушкаdried over Na2SO4
11. 11
    Концентрированиеconcentrated in vacuo
12. 12
    ДругоеThe residue was purified by flash chromatography

Методика

A flame-dried round-bottomed flask under N2 atmosphere was charged with 5-iodo-1,2,3-trimethoxybenzene (2.92 g, 9.93 mmol) and THF (31 mL) was added. The solution was cooled down to −78° C. and 1.5 M solution of t-BuLi in pentane (13.6 mL, 20.57 mmol) was added dropwise. The mixture was stirred for 1 h and transferred via canula to a precooled (−78° C.) solution of 6-nitroveratraldehyde (2.02 g, 9.57 mmol) in THF (12 mL) under N2 atmosphere. The resulting mixture was stirred for 2 h and slowly warmed up to 0° C., quenched with saturated aqueous solution of NH4Cl and allowed to warm-up to rt. Solvent was removed in vacuo and the residue was partitioned between water and DCM. Organic layer was collected and washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography using EtOAc/DCM (9:91) affording the title compound 241 (1.46 g, 40% yield) 1H NMR (CDCl3) δ (ppm): 7.61 (s, 1H), 7.16 (s, 1H), 6.58 (s, 2H), 6.45 (s, 1H), 6.09 (s, 1H), 3.97 (s, 3H), 3.93 (s, 3H), 3.84 (s, 3H), 3.83 (s, 6H). m/z: 402.4 (MH+).

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