Diisopropylamine → HCID 10467449, compound

HRID 1461266Notes

Reaction equation

HRID 1461266 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=1.[CH:13]([NH:16][CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[CH:13]([N:16]([CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=1)[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylate

Product 1

HCID 10467449HCID 10467449, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In 10 ml of toluene was dissolved 3.0 g (15.9 mmol) of ethyl 5-chloromethyl-2-furancarboxylate, followed by addition of 10 ml (71.5 mmol) of diisopropylamine. The mixture was heated at 100° C. for 48 hours. After cooling, the reaction mixture was filtered to remove the precipitate and the filtrate was concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (chloroform-methanol =20:1) to give 2.26 g (56.1%) of ethyl 5-diisopropylaminomethyl-2-furancarboxylate (Compound f) as light tan-colored oil.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customto remove the precipitate
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was then purified by silica gel column chromatography (chloroform-methanol =20:1)

Sources & evidence

ORD record
ord-21336513d5ea42fd9985a4447363e781
Source dataset
uspto-grants-1991_12
Patent number
US05075301

Reaction notes

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