Isobutylene oxide → HCID 86653375, compound

HRID 561258Notes

Reaction equation

HRID 561258 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[N-:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:2].[Li+].O1[C:19](C)([CH3:20])[CH2:18]1.[F:22][C:23]([F:36])([F:35])[S:24]([O:27]S(C(F)(F)F)(=O)=O)(=[O:26])=[O:25]>CCOCC>[O-:27][S:24]([C:23]([F:36])([F:35])[F:22])(=[O:26])=[O:25].[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[N+:11]1[C:19]([CH3:20])([CH3:18])[CH2:14][C:13]([CH3:23])([CH3:15])[CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11208Isobutylene oxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 58260902HCID 58260902, compound

Product 1

HCID 86653375HCID 86653375, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-80 °C

Procedure

Et2O (100 mL) was added to compound 2 (5.50 g, 26.3 mmol) to form a clear yellow solution. An Et2O (5 mL) solution of 1,2-epoxy-2-methylpropane (1.90 g, 26.3 mmol) was added dropwise over about 10 seconds, and the mixture was stirred overnight. The next day the mixture was cooled to −80° C. and trifluoromethanesulfonic anhydride (7.42 g, 26.3 mmol) was added dropwise. The mixture was warmed to ambient temperature over 1 hour. A thick suspension formed. After stirring for an additional hour, the solid was collected on a glass frit and washed with Et2O (3×15 mL). The solid was dried under reduced pressure. This was then extracted with CH2Cl2 (60 mL) and filtered through diatomaceous earth. The filter cake was washed with CH2Cl2 (2×30 mL). The combined CH2Cl2 extracts were evaporated to an oil and Et2O (15 mL) was added to cause a white crystalline solid to form. The solution was cooled to −10° C. overnight. The solid was then collected and dried under reduced pressure to afford 1.48 g of product. To obtain additional product the filter cake was loaded into a thimble. This was placed in a Soxhlet extractor and the solid was extracted with hot CH2Cl2 overnight. The resulting CH2Cl2 extract was evaporated and Et2O (10 mL) was added to afford additional product as off-white crystals. Total yield: 3.28 g, 30.6%. 1H NMR(C6D6): δ 7.21 (1H, d), 7.02 (2H, m), 2.47 (4H, q), 2.39 (1H, m), 1.11 (6H, t), 1.01 (6H, d).

Workup

  1. customto form a clear yellow solution
  2. temperatureThe mixture was warmed to ambient temperature over 1 hour
  3. customA thick suspension formed
  4. stirringAfter stirring for an additional hour
  5. customthe solid was collected on a glass frit
  6. washwashed with Et2O (3×15 mL)
  7. customThe solid was dried under reduced pressure
  8. extractionThis was then extracted with CH2Cl2 (60 mL)
  9. filtrationfiltered through diatomaceous earth
  10. washThe filter cake was washed with CH2Cl2 (2×30 mL)
  11. customThe combined CH2Cl2 extracts were evaporated to an oil and Et2O (15 mL)
  12. additionwas added
  13. customto form
  14. temperatureThe solution was cooled to −10° C. overnight
  15. customThe solid was then collected
  16. customdried under reduced pressure

Sources & evidence

ORD record
ord-9fa20d2129c14310a45bd24ceb838a27
Source dataset
uspto-grants-2011_11
Patent number
US08063232B2

Reaction notes

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