Ethylene Glycol → 2-((tert-Butyldiphenylsilyl)oxy)ethanol

HRID 870487Notes

Reaction equation

HRID 870487 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].N1C=CN=C1.[CH3:10][C:11]([Si:14](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:13])[CH3:12]>O1CCCC1>[Si:14]([O:3][CH2:2][CH2:1][OH:4])([C:11]([CH3:13])([CH3:12])[CH3:10])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 795ImidazoleHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 151562692-((tert-Butyldiphenylsilyl)oxy)ethanolYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a 2-L 3-necked round-bottom flask was placed tetrahydrofuran (800 mL), ethane-1,2-diol (40 g, 644.46 mmol, 1.00 equiv) and imidazole (61.4 g, 901.92 mmol, 1.40 equiv). This was followed by the addition of TBDPSCl (186.3 g) dropwise with stirring at 0° C. in 30 min. The resulting solution was stirred overnight at room temperature. The solids were filtered out, and the filtrate cake was washed with 200 mL of EA. The resulting mixture was washed with 200 mL of brine and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:25). Purification afforded 83 g (43%) of 2-[(tert-butyldiphenylsilyl)oxy]ethan-1-ol (85.2) as a colorless oil.

Workup

  1. customInto a 2-L 3-necked round-bottom flask was placed
  2. stirringThe resulting solution was stirred overnight at room temperature
  3. filtrationThe solids were filtered out
  4. washthe filtrate cake was washed with 200 mL of EA
  5. washThe resulting mixture was washed with 200 mL of brine
  6. concentrationconcentrated under vacuum
  7. customPurification

Sources & evidence

ORD record
ord-15f00605e12d47998dfd15dab0162309
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Reaction notes

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