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

HRID 1807058Notes

Reaction equation

HRID 1807058 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-330888b6efc94ac8ab53c204c54787cb
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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