Diethyl Ether → 4-(3,4-Dichlorophenyl)-3-(2-naphthylmethoxy)-2-butanol

HRID 52871

반응식

HRID 52871 반응식
[Si]([O:8][CH:9]([CH3:21])[CH:10]([OH:20])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)(C(C)(C)C)(C)C.[H-].[Na+].[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[CH2:34]Br.C(OCC)C>O1CCCC1.CN(C)C=O.O>[Cl:19][C:14]1[CH:13]=[C:12]([CH2:11][CH:10]([O:20][CH2:34][C:25]2[CH:26]=[CH:27][C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:24]=2)[CH:9]([OH:8])[CH3:21])[CH:17]=[CH:16][C:15]=1[Cl:18]

참가 물질

8

반응물 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 703202-BromomethylnaphthaleneHCID 190737393-(Tert-butyldimethylsilyloxy)-1-(3,4-dichlorophenyl)-2-butanol

생성물 1

HCID 190737424-(3,4-Dichlorophenyl)-3-(2-naphthylmethoxy)-2-butanol수율 18.5%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

2.32 g of the alcohol compound thus obtained was dissolved in a liquid mixture of 100 ml of tetrahydrofuran and 20 ml of dimethylformamide, and 0.34 g of 60% oily sodium hydride was added thereto with stirring under cooling with ice. The mixture was stirred at the same temperature for 30 minutes. Then, 1.47 g of 2-naphthylmethyl bromide was added thereto, and the mixture was stirred at room temperature for 20 hours. Then, ethyl ether and water were added to the reaction solution for liquid separation. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (hexane→hexane/ethyl acetate=50/1) for rough purification and then added to a liquid mixture of 100 me of tetrahydrofuran and 8 me of a 1M tetrahydrofuran solution of tetrabutylammonium fluoride. The mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure. Then, the residue was extracted by an addition of ethyl acetate and water. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=20/1→5/1) to obtain 0.46 g (yield: 18%) of 4-(3,4- dichlorophenyl)-3-(2-naphthylmethoxy)-2-butanol.

후처리

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringThe mixture was stirred at the same temperature for 30 minutes
  4. stirringthe mixture was stirred at room temperature for 20 hours
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe drying agent was separated by filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was subjected to silica gel column chromatography (hexane→hexane/ethyl acetate=50/1) for rough purification
  10. additionadded to a liquid mixture of 100 me of tetrahydrofuran and 8 me of a 1M tetrahydrofuran solution of tetrabutylammonium fluoride
  11. stirringThe mixture was stirred at room temperature for 3 hours
  12. concentrationThe reaction solution was concentrated under reduced pressure
  13. extractionThen, the residue was extracted by an addition of ethyl acetate and water
  14. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  15. dry with materialdried over anhydrous magnesium sulfate
  16. customThe drying agent was separated by filtration
  17. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-25d7de128b20496cb6f43fce52cdc313
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616803

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