Ethyl Acetate → HCID 22003490, 화합물

HRID 324177

반응식

HRID 324177 반응식
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]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 69720Trimethyl orthobeznoateHCID 516892Sodium BicarbonateHCID 22003462HCID 22003462, 화합물2회

생성물 1

HCID 22003490HCID 22003490, 화합물수율 78.4%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 962Water용매

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온도
150 °C

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-e28e0a4c74f4496e94cd8757a337ce1d
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218135B1

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