3,4-Dichlorobenzyl chloride → 3-(Tert-butyldimethylsilyloxy)-1-(3,4-dichlorophenyl)-2-butanol

HRID 52870

반응식

HRID 52870 반응식
[Mg].[Cl:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[Cl:11])[CH2:6]Cl.[Si:12]([O:19][CH:20]([CH3:23])[CH:21]=[O:22])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Cl-].[NH4+]>BrCCBr.C(OCC)C>[Si:12]([O:19][CH:20]([CH3:23])[CH:21]([OH:22])[CH2:6][C:5]1[CH:8]=[CH:9][C:10]([Cl:11])=[C:3]([Cl:2])[CH:4]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

참가 물질

7

반응물 4

HCID 76093,4-Dichlorobenzyl chlorideHCID 25517Ammonium ChlorideHCID 5462224Magnesium2회HCID 109322062-((Tert-butyldimethylsilyl)oxy)propanal

생성물 1

HCID 190737393-(Tert-butyldimethylsilyloxy)-1-(3,4-dichlorophenyl)-2-butanol수율 33.7%

시약·촉매·용매 2

HCID 78391,2-Dibromoethane촉매HCID 3283Diethyl Ether용매3회

실험 절차

2.45 g of magnesium (turnings) was added to 100 ml of ethyl ether, and a few drops of 1,2-dibromoethane were added thereto to activate magnesium. Then, 100 ml of an ethyl ether solution of 19.2 g of 3,4-dichlorobenzyl chloride was dropwise added thereto over a period of 3 hours with stirring under cooling with ice. Then, 50 ml of an ethyl ether solution of 6.11 g of 2-(tert-butyldimethylsilyloxy)propionaldehyde (which was produced by silylating ethyl 2-hydroxypropionate with tert-butyldimethylchlorosilane, followed by reducing with diisobutylaluminum hydride) was dropwise added to this solution over a period of 30 minutes with stirring under cooling with ice, and the mixture was stirred at the same temperature for 1 hour. Then, a saturated ammonium chloride aqueous solution was added thereto, and the mixture was further stirred at room temperature for 10 minutes. The organic layer was collected by separation, 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 to obtain 3.82 g (yield: 33%) of 3-(tert-butyldimethylsilyloxy)-1-(3,4-dichlorophenyl)-2-butanol.

후처리

  1. additionwere added
  2. temperatureunder cooling with ice
  3. stirringwith stirring
  4. temperatureunder cooling with ice
  5. stirringthe mixture was stirred at the same temperature for 1 hour
  6. stirringthe mixture was further stirred at room temperature for 10 minutes
  7. customThe organic layer was collected by separation
  8. washwashed with a saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe drying agent was separated by filtration
  11. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-75feed0703274784921d8c0456b5bb48
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616803

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