Dichloromethane → HCID 19774607, compound

HRID 1613922Notes

Reaction equation

HRID 1613922 reaction equation
C[O-].[Na+].O=[C:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:6][CH2:7][CH:8]=O.[CH:17]1[CH2:21][CH:20]=[CH:19][CH:18]=1.C(Cl)Cl>CO>[CH2:10]([C:5]1[CH:6]=[CH:7][CH:8]=[C:17]2[C:18]=1[CH:19]=[CH:20][CH2:21]2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7612CyclopentadieneHCID 10942334Sodium MethoxideHCID 131934644-Oxoundecanal

Product 1

HCID 19774607HCID 19774607, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

20.4 ml of a 30 percent strength solution of sodium methanolate (111 mmol) in methanol were initially introduced into the reaction vessel at 0° C., and a mixture of 9.0 g (44.5 mmol) of 4-oxoundecylaldehyde and 4.0 ml (49 mmol) of cyclopentadiene was added in the course of 30 minutes. After the mixture had been stirred at 0° C. for 2 hours and at room temperature for a further 3 hours, it was hydrolyzed, methylene chloride was added and the mixture was filtered over Corolite. The organic phase was separated off, dried over MgSO4 and evaporated. Column chromatography with hexane as the mobile phase gave 3.2 g (34%) of the indene 17. For the NMR data, see Table 1.

Workup

  1. additionwas added in the course of 30 minutes
  2. filtrationthe mixture was filtered over Corolite
  3. customThe organic phase was separated off
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-8f00b088d2f34ca3baa014eb7cc85157
Source dataset
uspto-grants-1993_03
Patent number
US05194619

Reaction notes

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