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

HRID 416266Notes

Reaction equation

HRID 416266 reaction equation
I[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=1.[Li]C(C)(C)C.CCCCC.[N+:24]([C:27]1[C:32]([CH:33]=[O:34])=[CH:31][C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=1)([O-:26])=[O:25]>C1COCC1>[CH3:38][O:37][C:29]1[C:30]([O:35][CH3:36])=[CH:31][C:32]([CH:33]([C:2]2[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=2)[OH:34])=[C:27]([N+:24]([O-:26])=[O:25])[CH:28]=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 885056-NitroveratraldehydeHCID 2981335-Iodo-1,2,3-trimethoxybenzeneHCID 178418306HCID 178418306, compound

Product 1

HCID 11143380(4,5-Dimethoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanolYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

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+).

Workup

  1. additionwas added
  2. stirringThe resulting mixture was stirred for 2 h
  3. temperatureslowly warmed up to 0° C.
  4. customquenched with saturated aqueous solution of NH4Cl
  5. temperatureto warm-up to rt
  6. customSolvent was removed in vacuo
  7. customthe residue was partitioned between water and DCM
  8. customOrganic layer was collected
  9. washwashed with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-783367f36b23490ba80fc014ca6e8f38
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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