Fumaryl chloride → HCID 13163692, compound

HRID 1742090Notes

Reaction equation

HRID 1742090 reaction equation
[C:1]([Cl:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([Cl:6])=[O:5]>CCOCC>[C@@H:2]1([C:1]([Cl:8])=[O:7])[CH2:4][CH:3]=[CH:2][CH2:1][C@H:3]1[C:4]([Cl:6])=[O:5]

Participants

3

Reactant 1

HCID 5325504Fumaryl chloride

Product 1

HCID 13163692HCID 13163692, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-50 °C

Procedure

Freshly distilled fumaryl dichloride (3.7 g; 24 mmol) is dissolved in 10 ml of dry Et2O in an oven dried 20-neck 50 ml round bottom flask, fitted with a gas inlet and dry ice Dewar condenser. The stirred solution is cooled to approximately -50° C. (dry ice/CH3CN). Butadiene (ca. 3 ml) is condensed into the flask and the cooling bath removed. Within 25-30 min the exothermic reaction ceases. After an additional 10 min the excess butadiene and solvent are removed in vacuo to furnish 4.7 g (approx 95%) of the Diels-Alder adduct as a colorless liquid which is used immediately without further purification. IR (neat) 3140 and 1785 cm-1.

Workup

  1. customdried 20-neck 50 ml round bottom flask
  2. customfitted with a gas inlet
  3. customcondensed into the flask
  4. customthe cooling bath removed
  5. customWithin 25-30 min the exothermic reaction ceases
  6. customAfter an additional 10 min the excess butadiene and solvent are removed in vacuo
  7. customto furnish 4.7 g (approx 95%) of the Diels-Alder adduct as a colorless liquid which
  8. customis used immediately without further purification

Sources & evidence

ORD record
ord-5e9fcf83c84b4fceb2fbd3ed7ac040a8
Source dataset
uspto-grants-1994_08
Patent number
US05336796

Reaction notes

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