Dimethyl Carbonate → (1S-trans)-Methyl 1-(1,3-benzodioxol-5-yl)-2,3-dihydro-3-oxo-5-propoxy-1H-indene-2-carboxylate

HRID 277493노트

반응식

HRID 277493 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@H:10]3[C:18]4[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH3:22])=[CH:16][CH:17]=4)[C:12](=[O:23])[CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[H-].[Na+].C[O-].[Na+].[C:29](=O)([O:32]C)[O:30][CH3:31]>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@H:10]3[C:18]4[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH3:22])=[CH:16][CH:17]=4)[C:12](=[O:23])[C@@H:11]3[C:29]([O:30][CH3:31])=[O:32])=[CH:9][C:4]=2[O:3][CH2:2]1

참가 물질

6

반응물 4

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 10942334Sodium MethoxideHCID 11833850(S)-3-(1,3-Benzodioxol-5-yl)-2,3-dihydro-6-propoxy-1H-inden-1-one

생성물 1

HCID 18683602(1S-trans)-Methyl 1-(1,3-benzodioxol-5-yl)-2,3-dihydro-3-oxo-5-propoxy-1H-indene-2-carboxylate수율 73%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
40 °C

실험 절차

A 100 mL three-necked flask under nitrogen was charged with (S)-3-(1,3-Benzodioxol-5-yl)-2,3-dihydro-6-propoxy-1H-inden-1-one (1.5 g, 4.84 mmol), toluene (20 mL), 60% NaH suspension (213 mg, 5.3 mmol), NaOMe (288 mg, 5.3 =mmol), and dimethyl carbonate (2.5 mL, 29 mmol). The solution was warmed to 40 ° C. for 3 h, cooled to 0° C., quenched with 3 M AcOH (0.5 mL) and diluted with H2O (50 mL) and EtOAc (50 mL). The organic phase was washed with brine (50 mL), dried (MgSO4) and concentrated. The crude material was triturated with EtOAc/hexane (1:3, 50 mL) affording (1S-trans)-methyl 1-(1,3-benzodioxol-5-yl) -2,3-dihydro-3-oxo-5-propoxy-1H-indene-2-carboxylate as a pale yellow solid (710 mg, 73% yield).

후처리

  1. temperaturecooled to 0° C.
  2. customquenched with 3 M AcOH (0.5 mL)
  3. additiondiluted with H2O (50 mL) and EtOAc (50 mL)
  4. washThe organic phase was washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude material was triturated with EtOAc/hexane (1:3, 50 mL)

출처 및 근거

ORD 기록
ord-5d19cae0007f4f1d9986d8dfe8ec88bf
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355813B1

반응 노트

불러오는 중…