Triethylamine → HCID 86587497, compound

HRID 987471Notes

Reaction equation

HRID 987471 reaction equation
[N+:1]([C:4]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[C:7]([O:13][CH3:14])=[C:6]([O:15][CH3:16])[CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH2:24]([O:31][CH2:32][C:33](Cl)=[O:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[CH2:24]([O:31][CH2:32][C:33]([O:10][C:9]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[C:8]=1[O:11][CH3:12])=[O:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 15662884HCID 15662884, compound

Product 1

HCID 86587497HCID 86587497, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Nitro-2,3,4-trimethoxyphenol (1.25 g) and triethylamine (1.12 mL) were dissolved in dichloromethane (20 mL), benzyloxyacetyl chloride (1.1 mL) was added dropwise to the solution under ice cooling, and the mixture was stirred for 2 hours as it is. The reaction mixture was extracted with chloroform, and the extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound. Yield: 1.38 g (66.5%).

Workup

  1. extractionThe reaction mixture was extracted with chloroform
  2. washthe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-e55e280f7b2440109c6198c1be296d34
Source dataset
uspto-grants-2003_10
Patent number
US06632810B2

Reaction notes

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