Dimethyl Sulfoxide → 2-(3-Pyridylcarbonyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene

HRID 35192

反応式

HRID 35192 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([OH:34])[C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:28]4([CH3:33])[O:32][CH2:31][CH2:30][O:29]4)[CH:24]=3)[CH:19]=2)[CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:28]4([CH3:33])[O:29][CH2:30][CH2:31][O:32]4)[CH:24]=3)[CH:19]=2)=[O:34])[CH:12]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15612241HCID 15612241、化合物

生成物 1

HCID 156122422-(3-Pyridylcarbonyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene収率 94%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 165 mg of oxalyl chloride in 20 ml of methylene chloride was cooled to -50° C., 203 mg of dimethylsulfoxide added dropwise, and the mixture stirred for 5 minutes. A solution of 321 mg of 2-[(3-pyridyl)hydroxymethyl]-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene in 10 ml of methylene chloride was then added dropwise and the mixture stirred at -50° C. for 15 minutes. Triethylamine (506 mg) was added at -50° C. and the mixture stirred for 5 minutes, then allowed to warm to room temperature. The solution was washed with water, dried over sodium sulfate and the solvent removed under reduced pressure to give 300 mg of 2-(3-pyridylcarbonyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene as an oil.

後処理

  1. stirringthe mixture stirred at -50° C. for 15 minutes
  2. stirringthe mixture stirred for 5 minutes
  3. washThe solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-e1cc8cae1f3b435b9663a6a648bee487
出典データセット
uspto-grants-1988_08
特許番号
US04766127

関連ノート

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