Hydrochloric Acid → Diethyl 5,6-indandicarboxylate

HRID 2111617Notes

Reaction equation

HRID 2111617 reaction equation
[C:1]([C:8]([O:10][CH2:11][CH3:12])=[O:9])#[C:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:13]#[C:14][CH2:15][CH2:16][CH2:17][C:18]#[CH:19].Cl>C1(C)C(C)=CC=CC=1.C(=[Co](=C=O)C1C=CC=C1)=O>[CH2:17]1[C:18]2[C:14](=[CH:13][C:1]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:19]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 69803Diethyl acetylenedicarboxylateHCID 3371211,6-Heptadiyne

Product 1

HCID 23084541Diethyl 5,6-indandicarboxylateYield 21.8%

Reagents, catalysts & solvents 2

HCID 178521473C7H5CoO2CatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
80 °C

Procedure

Diethyl acetylenedicarboxylate (1.0 ml, 6.3 mmol) and dicarbonylcyclopentadienylcobalt (0.1 ml, 0.62 mmol) were added dropwise to a solution of 1,6-heptadiyne (0.72 ml, 6.3 mmol) in xylene (5 ml), and stirred at 80° C. for 5 days. To the reaction solution was added dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated under reduced pressure, followed by purifying the residue by silica gel chromatography (chloroform, successively hexane:ethyl acetate=10:1) to give 0.36 g of diethyl 5,6-indandicarboxylate.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customby purifying the residue by silica gel chromatography (chloroform, successively hexane

Sources & evidence

ORD record
ord-165e40bab6624303bc3a726675beda39
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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