1,3-Propanediol → 3-[(Tert-butyldimethylsilyl)oxy]propan-1-ol

HRID 742545Notes

Reaction equation

HRID 742545 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][CH2:6][OH:7].[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]>O1CCCC1.C(OCC)(=O)C>[Si:8]([O:3][CH2:4][CH2:5][CH2:6][OH:7])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (0.1 mole) in anhydrous tetrahydrofuran (200 ml) cooled to 0° C., with stirring under an atmosphere of nitrogen is added a solution of 1,3-dihydroxypropane (0.1 mole) in tetrahydrofuran (150 ml) slowly over a period of 1 hour. Then a solution of tert-butyldimethylsilyl chloride (0.1 mole) in tetrahydrofuran (150 ml) is added slowly over a period of 1 hour. Stirring is continued for 6 hours. The mixture is then diluted with ethyl acetate (400 ml), washed with water (100 ml), brine (75 ml), dried and concentrated to afford the title compound.

Workup

  1. stirringStirring
  2. washwashed with water (100 ml), brine (75 ml)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-198989b2db3c4cc1a9560741b5a36fe1
Source dataset
uspto-grants-1996_09
Patent number
US05554746

Reaction notes

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