Ethyl Acetate → HCID 22003490, compound

HRID 324177

Reaction equation

HRID 324177 reaction equation
CO[C:3]([O:12][CH3:13])(OC)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:14][C:15]1[C:20]([O:21][CH3:22])=[CH:19][C:18]([C:23]2[O:27][CH2:26][C:25]([CH3:29])([CH3:28])[C:24]=2[C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:17]C=1O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>S(O)(C1C=CC(C)=CC=1)(=O)=O.O.O>[C:30]([C:24]1[C:25]([CH3:29])([CH3:28])[CH2:26][O:27][C:23]=1[C:18]1[CH:19]=[C:20]([O:21][CH3:22])[C:15]2[N:14]=[C:3]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)[O:12][C:13]=2[CH:17]=1)([CH3:33])([CH3:31])[CH3:32]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 69720Trimethyl orthobeznoateHCID 516892Sodium BicarbonateHCID 22003462HCID 22003462, compound2×

Product 1

HCID 22003490HCID 22003490, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To 1.00 mL (5.82 mmol) of trimethyl orthobenzoate was added 204 mg (0.70 mmol) of 5-(4-amino-3-hydroxy-5-methoxyphenyl)-4-t-butyl-3,3-dimethyl-2,3-dihydrofuran (Compound [61]), and the mixture was refluxed for 1.5 hours at 150° C. To this reaction mixture, 2.0 ml of ethyl acetate, and 0.2 ml of H2O, and 10.1 mg (0.05 mmol) of TsOH H2O was added and the mixture was refluxed for 1 hours at 97° C. The resulting mixture was poured in saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried with magnesium sulfate anhydride, and concentrated. The residue was applied to a silica gel column and the elution was carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=10:1) to obtain 207 mg of 4-t-butyl-5-(4-methoxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran (Compound [62]). Yield 78.4%.

Workup

  1. temperaturethe mixture was refluxed for 1 hours at 97° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried with magnesium sulfate anhydride
  5. concentrationconcentrated
  6. washthe elution
  7. additionwas carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-e28e0a4c74f4496e94cd8757a337ce1d
Source dataset
uspto-grants-2001_04
Patent number
US06218135B1

Linked notes

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