Isobutylene oxide → HCID 86653375, compound

HRID 1897628Notes

Reaction equation

HRID 1897628 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 EtherSolvent3×

Conditions

Temperature
-80 °C

Procedure

Et2O (100 mL) was added to compound B (5.50 g, 26.3 mmol) to form a clear yellow solution. A solution of 1,2-epoxy-2-methylpropane (1.90 g, 26.3 mmol) in Et2O (5 mL) was added dropwise over about 10 seconds, and the mixture was stirred overnight. The mixture was then 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, a solid was collected on a glass frit and washed with Et2O (3×15 mL). The solid was dried under reduced pressure. The dried solid 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 which caused a white crystalline solid to form. The ether solution was cooled to −10° C. overnight. The white solid was then collected and dried under reduced pressure to afford 1.48 g of product C. 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. The combined yield of compound C was 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. customa solid was collected on a glass frit
  6. washwashed with Et2O (3×15 mL)
  7. customThe solid was dried under reduced pressure
  8. extractionThe dried solid 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 which
  13. customto form
  14. customThe white solid was then collected
  15. customdried under reduced pressure

Sources & evidence

ORD record
ord-2f275e7e951e4b3e95830b42c746dfc2
Source dataset
uspto-grants-2013_08
Patent number
US08519147B2

Reaction notes

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