Pyridine → Trimethylsilyl 10-undecenoate

HRID 2399695Notes

Reaction equation

HRID 2399695 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].N1C=CC=CC=1.[CH3:20][Si:21](Cl)([CH3:23])[CH3:22]>C1(C)C=CC=CC=1>[CH3:20][Si:21]([O:12][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5634Undecylenic AcidHCID 6397Chlorotrimethylsilane

Product 1

HCID 552417Trimethylsilyl 10-undecenoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a 3-liter, 3-neck flask equipped with an addition funnel, mechanical stirrer and reflux condenser were added undecylenic acid (Lucidol, 480 grams, 2.6 mol), pyridine (240 grams, 3.03 mol) and toluene (900 milliliters). Trimethylsilyl chloride (326 grams, 3.0 mol) was then added slowly via the addition funnel over 2.5 hours. After stirring at 25° C. for 16 hours, the precipitate was filtered off and washed with toluene. The flitrates were combined and the toluene was removed using a rotary evaporator. The residue was distilled through a packed column under reduced pressure and four fractions were collected. A first cut was collected between 25° C. and 115° C. at 1 millimeter of mercury. A second cut was collected between 115° C. and 119° C. at 1 millimeter of mercury. The third cut, collected between 115° C. and 120° C. at 1 millimeter of mercury, was identified by infrared spectroscopy, and with 13C and 1H NMR spectrometries as the trimethylsilyl ester of undecylenic acid (320.4 grams). A fourth cut, collected between 115° C. and 121° C. at 1 millimeter of mercury, was a light-yellow oil. There was no evidence of free acid in fraction 3 using infrared spectroscopy. The carboxylic acid infrared absorption of undecylenic acid was found at 1,720 cm-1. The trimethylsilyl ester group absorbed at 1,640 cm-1.

Workup

  1. customTo a 3-liter, 3-neck flask equipped with an addition funnel, mechanical stirrer
  2. temperaturereflux condenser
  3. filtrationthe precipitate was filtered off
  4. washwashed with toluene
  5. customthe toluene was removed
  6. customa rotary evaporator
  7. distillationThe residue was distilled through a packed column under reduced pressure and four fractions
  8. customwere collected
  9. customA first cut was collected between 25° C. and 115° C. at 1 millimeter of mercury
  10. customA second cut was collected between 115° C. and 119° C. at 1 millimeter of mercury
  11. customThe third cut, collected between 115° C. and 120° C. at 1 millimeter of mercury
  12. customA fourth cut, collected between 115° C. and 121° C. at 1 millimeter of mercury
  13. customabsorption of undecylenic acid
  14. customThe trimethylsilyl ester group absorbed at 1,640 cm-1

Sources & evidence

ORD record
ord-72ee5ac6d5c14e7abe0c553cd66f87dd
Source dataset
uspto-grants-1995_09
Patent number
US05451483

Reaction notes

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