Propylene Glycol → 1-((Tert-butyldimethylsilyl)oxy)propan-2-ol

HRID 521175Notes

Reaction equation

HRID 521175 reaction equation
[CH2:1]([OH:5])[CH:2]([OH:4])[CH3:3].[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].CCN(C(C)C)C(C)C>C(Cl)Cl.CCOCC>[Si:10]([O:5][CH2:1][CH:2]([OH:4])[CH3:3])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 1030Propylene GlycolHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 131751341-((Tert-butyldimethylsilyl)oxy)propan-2-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of propylene glycol (1.0 g, 13 mmol) in DCM (60.0 mL) was added tert-butyldimethylchlorosilane (2.0 g, 13 mmol) followed by DIPEA (3.2 mL, 18 mmol). The reaction mixture was stirred at ambient temperature for 18 hours. The solution was diluted with ether, washed with saturated aqueous NaHCO3, brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford the title compound.

Workup

  1. washwashed with saturated aqueous NaHCO3, brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51591661a1e145398e734a4d0f0936fb
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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