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

HRID 989677Notes

Reaction equation

HRID 989677 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[H-].[Na+].[C:8]([Si:12]([CH3:15])([CH3:14])Cl)([CH3:11])([CH3:10])[CH3:9]>C1COCC1>[CH3:14][Si:12]([CH3:15])([C:8]([CH3:11])([CH3:10])[CH3:9])[O:4][CH2:3][CH2:2][CH2:1][OH:5]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1,3-propanediol (4.8 mL, 66 mmol) in THF (100 mL) was added sodium hydride (60% dispersion in mineral oil, 2.6 g, 66 mmol) followed by tert-butyldimethyl chlorosilane. The solution was allowed to stir for 16 h, and concentrated to an oily residue. Purification by chromatography (40% ethyl acetate in hexanes) afforded title compound (12.3 g). MS (M+H): 191.

Workup

  1. concentrationconcentrated to an oily residue
  2. customPurification by chromatography (40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4eb15a6fe62345f6b6e0f1137ed38f70
Source dataset
uspto-grants-2002_10
Patent number
US06458783B1

Reaction notes

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