Ethyl Acetate → HCID 45092074, compound

HRID 525351Notes

Reaction equation

HRID 525351 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])C)C(O)(C)C.CC(C)([O-])C.[K+].CCOC(C)=O>C1COCC1.CCCCCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:16]([CH3:18])([CH3:19])[O:15][C:14](=[O:20])[NH:13]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 89827431HCID 89827431, compound

Product 1

HCID 45092074HCID 45092074, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of tert-butyl (1-(2-fluorophenyl)-2-hydroxy-2-methylpropyl)carbamate (400 mg, 1.41 mmol) in THF (8 mL) was added potassium tert-butoxide (316.87 mg, 2.82 mmol) at 0-5° C. The resulting reaction mixture was stirred for 2 hours at ambient temperature. After completion of the reaction (monitored by TLC, TLC system: 50% EtOAc in hexane), the reaction mixture was quenched with ice water and extracted with EtOAc. The combined organic layers were washed with, water, saturated NaCl solution and dried on Na2SO4, filtered, and concentrated under reduced pressure to afford 4-(2-fluorophenyl)-5,5-dimethyloxazolidin-2-one (290 mg, 98.18%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.05 (s, 1H), 7.44-7.35 (m, 2H), 7.30-7.22 (m, 2H), 4.88 (s, 1H), 1.53 (s, 3H), 0.88 (s, 3H). m/z (ESI) 210.1 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. customthe reaction mixture was quenched with ice water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with, water, saturated NaCl solution
  5. customdried on Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e103b8d826e64ec78f57be63b2010e06
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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