Dimethyl Sulfate → HCID 86747857, compound

HRID 1033767Notes

Reaction equation

HRID 1033767 reaction equation
[H-].[Na+].[OH:3][CH2:4]/[CH:5]=[C:6](/[CH2:8][CH2:9]/[CH:10]=[C:11](/[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])\[CH3:12])\[CH3:7].Cl[CH2:20][C:21]([O-:23])=[O:22].[Na+].[CH3:25]OS(OC)(=O)=O>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C.CN(C)C=O>[CH3:7]/[C:6](/[CH2:8][CH2:9]/[CH:10]=[C:11](\[CH3:12])/[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:5]\[CH2:4][O:3][CH2:20][C:21]([O:23][CH3:25])=[O:22]

Participants

9

Reactant 4

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 445070FarnesolHCID 23665759Sodium chloroacetate

Product 1

HCID 86747857HCID 86747857, compoundYield 106.3%

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3.60 g (90 mmol, 2 equiv) of 60% NaH in mineral oil, washed three times with pentane, in 170 mL of tetrahydrofuran at room temperature under argon was added a solution of 10.00 g (45 mmol) of E,E-farnesol in 30 mL of tetrahydrofuran, and the resulting mixture was heated at reflux for 0.5 hours. After having cooled to room temperature the reaction was treated with 1.66 g (4.5 mmol, 10%) of tetra-n-butylammonium iodide and 5.50 g (47.5 mmol, 1.05 eq.) of the sodium chloroacetate, and heated to reflux for 20 hours. The mixture was cooled to 0° C. and 200 mL of dimethylformamide was slowly added, followed by 9.4 mL (99 mmol, 2.2 eq.) of dimethylsulfate. After four hours, the reaction was diluted with 600 mL of 1:1 diethyl ether:hexane, washed with five 100 mL portions of H2O and 100 mL of brine, dried over MgSO4, and evaporated to afford 14.09 g of a dark yellow oil. Purification by flash chromatography on 1000 g of Merck 9385 silica, eluted with 5:95 ethyl acetate:hexane provided 10.19 g (77%) of title ester as a yellow oil.

Workup

  1. washwashed three times with pentane
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux for 0.5 hours
  4. temperatureheated
  5. temperatureto reflux for 20 hours
  6. temperatureThe mixture was cooled to 0° C.
  7. washhexane, washed with five 100 mL portions of H2O and 100 mL of brine
  8. dry with materialdried over MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-b5731dd2b018496fa38eabe540ca1968
Source dataset
uspto-grants-1994_05
Patent number
US05312814

Reaction notes

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