p-Toluenesulfonic acid monohydrate → tert-butyl-dimethyl-[2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethoxy]-silane

HRID 1807058노트

반응식

HRID 1807058 반응식
[C:1]([Si:5]([CH3:16])([CH3:15])[O:6][CH2:7][CH2:8][C@H:9]([OH:14])[C:10]([CH3:13])([OH:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].O.[C:18]1(C)[CH:23]=CC(S(O)(=O)=O)=C[CH:19]=1>COC(OC)(C)C>[C:1]([Si:5]([CH3:15])([CH3:16])[O:6][CH2:7][CH2:8][C@H:9]1[C:10]([CH3:11])([CH3:13])[O:12][C:18]([CH3:23])([CH3:19])[O:14]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 71545770(S)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentane-2,3-diol

생성물 1

HCID 67299820tert-butyl-dimethyl-[2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethoxy]-silane수율 1,503.3%

시약·촉매·용매 1

HCID 64952,2-Dimethoxypropane용매

실험 절차

Step E To a suspension of (S)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentane-2,3-diol (6.8 g, 27 mmol) in 2,2-dimethoxypropane (35 mL) was added p-toluenesulfonic acid monohydrate (0.2 g). The reaction mixture was stirred at room temperature for 30 min. The mixture was partitioned between water and dichloromethane. The organic layer was separated, the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:20) to give tert-butyl-dimethyl-[2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethoxy]-silane as a yellow oil (4.56 g, 58%).

후처리

  1. customThe mixture was partitioned between water and dichloromethane
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (EtOAc:hexanes=1:20)

출처 및 근거

ORD 기록
ord-330888b6efc94ac8ab53c204c54787cb
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354444B2

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