Dimethyl Sulfate → HCID 21831733, compound

HRID 1601478Notes

Reaction equation

HRID 1601478 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:10]([Li])[CH2:11][CH2:12][CH3:13].[CH2:15]([CH:17]1[O:19][CH2:18]1)Br.S(OC)(OC)(=O)=O.[Cl-].[NH4+].[CH3:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>O1CCCC1>[CH2:10]1[C:30]2[C:31](=[CH:32][CH:33]=[CH:34][CH:29]=2)[C:12]([CH2:13][CH:17]([O:19][CH3:18])[CH2:15][C:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH:2]=2)=[CH:11]1

Participants

8

Reactant 6

HCID 6497Dimethyl SulfateHCID 7219IndeneHCID 8058HexaneHCID 18430EpibromohydrinHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 21831733HCID 21831733, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 23.2 g of indene dissolved in 200 mL tetrahydrofuran chilled to -78° C. under argon was added 80 mL of butyl lithium (2.5M in hexanes). The resulting solution was warmed to room temperature for one hour and then re-chilled to -78° C. To this solution was added 13.7 g epibromohydrin. After stirring for one hour at -78° C., the solution was brought to room temperature for one hour and then refluxed for one hour. After cooling, 12.6 g of dimethyl sulfate was added and this mixture was refluxed for 48 hours. Hexane and saturated ammonium chloride were then added and the organic layer recovered. After further washing the organic layer with brine, it was dried over MgSO4 and evaporated to an oil. A portion of this oil was chromatographed to provide 1,3-bis(3-indenyl)-2-methoxypropane as a pale yellow oil.

Workup

  1. temperatureThe resulting solution was warmed to room temperature for one hour
  2. temperaturere-chilled to -78° C
  3. waitthe solution was brought to room temperature for one hour
  4. temperaturerefluxed for one hour
  5. temperatureAfter cooling
  6. temperaturethis mixture was refluxed for 48 hours
  7. customthe organic layer recovered
  8. washAfter further washing the organic layer with brine, it
  9. dry with materialwas dried over MgSO4
  10. customevaporated to an oil
  11. customA portion of this oil was chromatographed

Sources & evidence

ORD record
ord-2885d4583aea4c76ac8fafe0611c2d48
Source dataset
uspto-grants-1999_11
Patent number
US05977270

Reaction notes

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