Dichloromethane → 5-(4-Hydroxybenzyl)-3-trityloxazolidine-2,4-dione

HRID 1595480ノート

反応式

HRID 1595480 の反応式
[C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:29]2[O:33][C:32](=[O:34])[NH:31][C:30]2=[O:35])=[CH:24][CH:23]=1.ClCCl>O.C(OCC)(=O)C.C(N(CC)CC)C.CN(C)C=O>[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:31]2[C:30](=[O:35])[CH:29]([CH2:28][C:25]3[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][CH:24]=3)[O:33][C:32]2=[O:34])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 3

HCID 6344DichloromethaneHCID 6456Trityl chlorideHCID 103529685-([4-Hydroxyphenyl]methyl)oxazolidine-2,4-dione

生成物 1

HCID 149136625-(4-Hydroxybenzyl)-3-trityloxazolidine-2,4-dione収率 60.3%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

0.33 g (1.18 mmole) triphenylmethyl chloride was added to a solution of 0.245 g (1.18 mmole) 5-([4-hydroxyphenyl]methyl)oxazolidine-2,4-dione, 0.165 ml (1.18 mmole) triethylamine, 5 ml dichloromethane and 5 ml dimethylformamide on an icebath. The temperature of the reaction mixture was allowed to reach room temperature. After 1.5 hours 0.05 ml more triethylamine was added. After 2 hours ethyl acetate and water were added and the phases were seperated. The organic phase was dried (sodium sulfate), the solvent was evaporated and the crude product was purified by chromatography on silica gel using heptane:ethyl acetate (3:2) as eluent to give 0.32 g (yield 60%) 3-triphenylmethyl-5-([4-hydroxyphenyl]methyl)oxazolidine-2,4-dione.

後処理

  1. customto reach room temperature
  2. customthe phases were seperated
  3. dry with materialThe organic phase was dried (sodium sulfate)
  4. customthe solvent was evaporated
  5. customthe crude product was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-2e8117331b8542f9ad8c12deb457a29f
出典データセット
uspto-grants-2001_09
特許番号
US06288096B1

反応ノート

読み込み中…