Sodium hydride → HCID 9801173、化合物

HRID 2293602ノート

反応式

HRID 2293602 の反応式
[CH2:1]1[O:32][C:31]2[CH:30]=[CH:29][C:5]([CH2:6][N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)=[C:8]3[C:24]([O:26]CC)=[O:25])=[CH:4][C:3]=2[O:2]1.COC1C=CC(C2C3C(=CC=CC=3)NC=2C(OCC)=O)=CC=1.[H-].[Na+].C(Cl)C1C=CC2OCOC=2C=1>CN(P(N(C)C)(N(C)C)=O)C>[CH2:1]1[O:32][C:31]2[CH:30]=[CH:29][C:5]([CH2:6][N:7]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:9]([C:16]4[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=4)=[C:8]3[C:24]([OH:26])=[O:25])=[CH:4][C:3]=2[O:2]1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 21476961HCID 21476961、化合物HCID 22676729HCID 22676729、化合物

生成物 1

HCID 9801173HCID 9801173、化合物収率 66%

試薬・触媒・溶媒 1

HCID 12679Hexamethylphosphoramide溶媒2 回

実験手順

Ethyl 1-(3,4-methylenedioxybenzyl)-3-(4-methoxyphenyl)indole-2-carboxylate. To a solution of ethyl 3-(4-methoxyphenyl)indole-2-carboxylate (110 mg, 0.37 mmol) in HMPA (2 mL) stirred at ice bath temperature under an argon atmosphere was added NaH (14 mg of 80% oil dispersion, 0.46 mmol, oil removed by pentane wash). After 15 min a solution of piperonyl chloride (128 mg, 0.75 mmol) in HMPA (0.5 mL) was added and the ice bath removed. The reaction mixture was stirred 7 h at room temperature then partitioned between 3N HCl (25 mL) and EtOAc (50 mL). The organic extract was washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl and dried (Na2SO4). The solvent was removed in vacuo. The residue was purified by chromatography (silica gel, gradient elution from 25% Et2O/hexanes to 45% Et2O/hexanes) to afford the title compound (105 mg, 66%)

後処理

  1. customthe ice bath removed
  2. customthen partitioned between 3N HCl (25 mL) and EtOAc (50 mL)
  3. extractionThe organic extract
  4. washwas washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuo
  7. customThe residue was purified by chromatography (silica gel, gradient elution from 25% Et2O/hexanes to 45% Et2O/hexanes)

出典と根拠

ORDレコード
ord-5f81704b5caa445e91b52557355af056
出典データセット
uspto-grants-1997_11
特許番号
US05686481

反応ノート

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