Dimethyl Sulfoxide → (1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanone

HRID 890068ノート

反応式

HRID 890068 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH:24]([CH:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][O:27]2)[OH:25])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([N:18]1[CH2:19][CH2:20][CH:21]([C:24]([CH:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][O:27]2)=[O:25])[CH2:22][CH2:23]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22248465(1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol

生成物 1

HCID 22248144(1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanone収率 87.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

After adding 0.511 ml of dimethylsulfoxide dropwise to a dichloromethane solution (15 ml) containing 0.315 ml of oxalyl chloride at −70° C., the mixture was stirred for 10 minutes, a solution of 597 mg of (1-benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanol in dichloromethane (5 ml) was added dropwise, and stirring was continued for 1 hour. Next, 2.5 ml of triethylamine was added dropwise to the reaction solution, the cooling bath was removed, and the mixture was stirred at room temperature. Water was added to the reaction solution, and extraction was is performed with ethyl acetate. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain the title compound (517 mg, 33% yield).

後処理

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. customthe cooling bath was removed
  4. stirringthe mixture was stirred at room temperature
  5. additionWater was added to the reaction solution, and extraction
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-29889e375efc40a0b71c63ca6bfbdef9
出典データセット
uspto-grants-2006_02
特許番号
US06995144B2

反応ノート

読み込み中…