Dimethylformamide → HCID 86730337, compound

HRID 1427034Notes

Reaction equation

HRID 1427034 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5]Br)[CH3:2].[OH:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[OH:16])[CH:11]=[O:12].C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>Cl.C(OCC)(=O)C.O>[CH2:1]([O:3][CH2:4][CH2:5][O:16][C:15]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][C:8]=1[OH:7])[CH3:2]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 87683,4-DihydroxybenzaldehydeHCID 10340Sodium CarbonateHCID 611412-Bromoethyl ethyl ether

Product 1

HCID 86730337HCID 86730337, compoundYield 28.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Commercially available 2-bromoethyl ethyl ether (33.8 g, 221 mmol) was added to a solution of commercially available 3,4-dihydroxybenzaldehyde (30.5 g, 221 mmol) and sodium carbonate (35.1 g, 331 mmol) in NP-dimethylformamide (310 mL) under nitrogen atmosphere at mom temperature. The liquid mixture was stirred at room temperature for 5 days. The reaction liquid was cooled to 0° C. and diluted with 2 M hydrochloric acid, ethyl acetate, and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed serially with water and a saturated saline solution and then dried over anhydrous magnesium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. The insoluble matters were separated by filtration with dichloromethane and the raw material was removed. The filtrate was purified with silica gel column chromatography (n-heptane:ethyl acetate=17:3-1:1) to obtain the title compound (13.2 g, 28%).

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to 0° C.
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed serially with water
  5. dry with materiala saturated saline solution and then dried over anhydrous magnesium sulfate
  6. customThe drying agent was separated by filtration
  7. concentrationthe filtrate was concentrated under vacuum
  8. customThe insoluble matters were separated by filtration with dichloromethane
  9. customthe raw material was removed
  10. customThe filtrate was purified with silica gel column chromatography (n-heptane:ethyl acetate=17:3-1:1)

Sources & evidence

ORD record
ord-9e0da0fb683b4ac28f12820ce8ed655c
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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