Ethyl Acetate → HCID 22003490、化合物

HRID 324177ノート

反応式

HRID 324177 の反応式
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]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 69720Trimethyl orthobeznoateHCID 516892Sodium BicarbonateHCID 22003462HCID 22003462、化合物2 回

生成物 1

HCID 22003490HCID 22003490、化合物収率 78.4%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-e28e0a4c74f4496e94cd8757a337ce1d
出典データセット
uspto-grants-2001_04
特許番号
US06218135B1

反応ノート

読み込み中…