Hydrogen Peroxide → 3-(6-Bromo-2-((tert-butyldimethylsilyl)oxy)-3-chloro-4-(4-methoxybenzyl)phenyl)propan-1-ol

HRID 576403노트

반응식

HRID 576403 반응식
[CH2:1]([C:4]1[C:17]([Br:18])=[CH:16][C:15]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:14]([Cl:28])[C:5]=1[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])[CH:2]=[CH2:3].CSC.B.[OH-:33].[Na+].OO>C1COCC1.O>[Br:18][C:17]1[C:4]([CH2:1][CH2:2][CH2:3][OH:33])=[C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:8])[CH3:9])[C:14]([Cl:28])=[C:15]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[CH:16]=1

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 86714082(2-Allyl-3-bromo-6-chloro-5-(4-methoxybenzyl)phenoxy)(tert-butyl)dimethylsilane

생성물 1

HCID 867140833-(6-Bromo-2-((tert-butyldimethylsilyl)oxy)-3-chloro-4-(4-methoxybenzyl)phenyl)propan-1-ol수율 65%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of bromide 186 (2.57 g, 5.33 mmol) in THF (35 mL) was added borane dimethylsulfide complex (10M in THF, 0.18 mL, 1.76 mmol) at 0° C. The mixture was stirred at rt for 1 hr. The mixture was cooled to 0° C. and H2O (0.5 mL), aq. 3N NaOH solution (1.1 mL), 35% H2O2 (0.65 mL) were added to the mixture.) The mixture was stirred at 50° C. for 30 min and cooled to rt. The mixture was extracted with EtOAc/aq. 50% NaCl solution (100 mL/100 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 187 (1.73 g, 65%).

후처리

  1. temperatureThe mixture was cooled to 0° C.
  2. stirring) The mixture was stirred at 50° C. for 30 min
  3. temperaturecooled to rt
  4. extractionThe mixture was extracted with EtOAc/aq
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-0135ba4ff9824129a752feb07967fa9e
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034921B2

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