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

HRID 277493ノート

反応式

HRID 277493 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
40 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5d19cae0007f4f1d9986d8dfe8ec88bf
出典データセット
uspto-grants-2002_03
特許番号
US06355813B1

反応ノート

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