Ethanol → HCID 59473796, compound

HRID 2069853Notes

Reaction equation

HRID 2069853 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[O:13]CC(C)(C)N=2)=[C:7]([CH:19]2[O:24]CCC[O:20]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)C.S(=O)(=O)(O)O>O>[C:1]([C:5]1[CH:6]=[C:7]2[C:8](=[C:9]([F:11])[CH:10]=1)[C:12](=[O:13])[O:20][CH:19]2[OH:24])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 594737622-(4-Tert-butyl-2-1,3-dioxinan-2-yl-6-fluoro-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole

Product 1

HCID 59473796HCID 59473796, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.8 g (5.4 mmol) of 2-(4-tert-butyl-2-1,3-dioxinan-2-yl-6-fluoro-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole was weighed into a 200 mL round bottom flask fitted with a stir bar and reflux condenser. Added 75 mL of ethanol and stirred to obtain a clear solution. Added 50 mL of 50% aqueous sulfuric acid. Stirred at reflux for 18 h. Poured the reaction mixture into 400 mL water. Extracted the aqueous mixture with 2×200 mL CH2Cl2. Combined the organic extracts and washed with 200 mL brine. Dried over Na2SO4 and removed the solvent on rotavap. Dried under high vacuum to obtain 1.29 g of the title compound as on off-white solid. MS (ESI) 223 (M−H)−.

Workup

  1. customfitted with a stir bar
  2. temperaturereflux condenser
  3. customto obtain a clear solution
  4. stirringStirred
  5. temperatureat reflux for 18 h
  6. extractionExtracted the aqueous mixture with 2×200 mL CH2Cl2
  7. washwashed with 200 mL brine
  8. dry with materialDried over Na2SO4
  9. customremoved the solvent on rotavap
  10. customDried under high vacuum

Sources & evidence

ORD record
ord-386aab32d5f74f55a9acabb2eeda2d73
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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