Sodium Chloride → 3-[(Tert-butyldimethylsilyl)oxy]propan-1-ol

HRID 1708079Notes

Reaction equation

HRID 1708079 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][OH:6].[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[Cl-].[Na+]>O1CCCC1.CCOCC>[Si:8]([O:6][CH2:5][CH2:4][CH2:3][OH:7])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-olYield 83%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (6.29 g, 262 mmol) in dry tetrahydrofuran (400 ml) was added 1,3-propanediol (20.0 g, 262 mmol) over 5 min and the mixture was stirred at room temperature under dry nitrogen for 1.5 hr. t-Butyldimethylsilyl chloride (39.5 g, 262 mmol) was added portionwise and the mixture was stirred at room temperature for 1.5 hr. Saturated sodium chloride solution (300 ml) then ether (500 ml) were added. The organic portion was dried (magnesium sulphate), filtered and the solvent removed. The residue was purified by column chromatography on silica gel eluting with ether-hexane (1:2, 3:2) to afford 3-(t-butyldimethylsilyloxy)propan-1-ol as a colourless liquid (41.2 g, 83%); δH (CDCl3) 0.10 (6H, s, CH3), 0.93 (9H, s, C(CH3)3), 1.80 (2H, qu, J 6 Hz, CH2), 2.37 (1H, br.s, OH), 3.87 ( 4H, m, CH2O ).

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hr
  2. dry with materialThe organic portion was dried (magnesium sulphate)
  3. filtrationfiltered
  4. customthe solvent removed
  5. customThe residue was purified by column chromatography on silica gel eluting with ether-hexane (1:2, 3:2)

Sources & evidence

ORD record
ord-1d0d3a023dab4564bca66c7854681285
Source dataset
uspto-grants-1994_10
Patent number
US05356886

Reaction notes

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