Hydrochloric Acid → 3-[(Tert-butyldimethylsilyl)oxy]propan-1-ol

HRID 48086

Reaction equation

HRID 48086 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].N1C=CN=C1.Cl>CN(C=O)C>[O:4]([CH2:3][CH2:2][CH2:1][OH:5])[Si:10]([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 104421,3-PropanediolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,3-propanediol (10 mmol), tert-butyldimethylchlorosilane (11 mmol), and imidazole (22 mmol) dissolved in 5 mL of DMF was stirred at room temperature for 16 hours. The mixture was poured into 0.1 M HCl (100 mL) and extracted with ether (3×100 mL). The organic phases were washed with brine (100 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The mixture was purified by flash chromatography to give the product as a colorless oil.

Workup

  1. extractionextracted with ether (3×100 mL)
  2. washThe organic phases were washed with brine (100 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-3c0d0e4f28e3497f83930e61cad01c92
Source dataset
uspto-grants-2004_03
Patent number
US06702705B1

Linked notes

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