Potassium Carbonate → HCID 11106784, compound

HRID 1793779Notes

Reaction equation

HRID 1793779 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][CH:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:18])=[C:14]([OH:17])[CH:15]=2)[CH2:10][CH2:9]1.Cl[CH2:20][C:21]([CH2:23]Cl)=[CH2:22]>O1CCOCC1>[CH3:7][CH:8]1[C:16]2[CH:15]=[C:14]3[O:17][CH2:22][C:21](=[CH2:20])[CH2:23][O:18][C:13]3=[CH:12][C:11]=2[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 158593-Chloro-2-chloromethyl-1-propeneHCID 12084175HCID 12084175, compound

Product 1

HCID 11106784HCID 11106784, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 25.7 g (186 mmol) of potassium carbonate were heated to reflux with stirring. At this temperature, over the course of 5 h, a mixture of 15.3 g (93.2 mmol) of 1-methylindane-5,6-diol and 11.6 g (92.8 mmol) of 3-chloro-2-chloromethylprop-1-ene dissolved in 50 ml of dioxane was added dropwise. When addition was complete, the mixture was stirred for a further 1 h under reflux and the inorganic solids precipitated out were filtered off with suction after cooling the reaction mixture. The solids were washed with acetone and the combined organic phases freed from solvent on a rotary evaporator. After flash chromatography (pentane/ether, 19:1, Rf=0.66) on silica gel, 7.3 g (36%) of 1-methyl-7-methylene-2,3,7,8-tetrahydro-1H,6H-5,9-dioxacyclohepta[f]indene were obtained.

Workup

  1. temperaturewere heated
  2. temperatureto reflux
  3. additionwas added dropwise
  4. additionWhen addition
  5. stirringthe mixture was stirred for a further 1 h
  6. temperatureunder reflux
  7. customthe inorganic solids precipitated out
  8. filtrationwere filtered off with suction
  9. temperatureafter cooling the reaction mixture
  10. washThe solids were washed with acetone
  11. customthe combined organic phases freed from solvent on a rotary evaporator

Sources & evidence

ORD record
ord-e1db4a44e7e14544b63782be2f909d07
Source dataset
uspto-grants-2006_04
Patent number
US07022664B2

Reaction notes

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