Potassium Carbonate → HCID 11106784, compound

HRID 1767441Notes

Reaction equation

HRID 1767441 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-d18929e3836b4b42b8dbe6d9a82753b7
Source dataset
uspto-grants-2007_06
Patent number
US07235519B2

Reaction notes

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