5-(Chloromethyl)-1,2,3-trimethoxybenzene → HCID 22344712, compound

HRID 1059854Notes

Reaction equation

HRID 1059854 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[Na+].Cl[CH2:17][C:18]1[CH:19]=[C:20]([O:28][CH3:29])[C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=1>CN(C=O)C>[CH3:25][O:24][C:22]1[CH:23]=[C:18]([CH2:17][S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=2)(=[O:11])=[O:10])[CH:19]=[C:20]([O:28][CH3:29])[C:21]=1[O:26][CH3:27]

Participants

4

Reactant 2

HCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 102438505HCID 102438505, compound

Product 1

HCID 22344712HCID 22344712, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

A suspension of Example 96A (380 mg, 1.6 mmol) in DMF (10 mL) was treated slowly with a solution of 5-(chloromethyl)-1,2,3-trimethoxybenzene (344 mg, 1.6 mmol) in DMF (5 mL), heated to 120° C. for hour, cooled to room temperature, and partitioned between ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate, and the combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/dichloromethane to provide the desired product.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and brine
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-b06d91dd34db4a5ca8090a3905d1df15
Source dataset
uspto-grants-2003_02
Patent number
US06521658B1

Reaction notes

Loading…