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

HRID 1595480노트

반응식

HRID 1595480 반응식
[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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2e8117331b8542f9ad8c12deb457a29f
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288096B1

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