Ethylene Glycol → 2-(tert-Butyl(dimethyl)silyl)oxyethanol

HRID 21420Notes

Reaction equation

HRID 21420 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:9]([OH:12])[CH2:10][OH:11].C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[Si:1]([O:11][CH2:10][CH2:9][OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanol

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyldimethylsilylchloride (100 g, 0.66M) in dry dichloromethane (70 ml) was added, drop-wise, to a stirred mixture of distilled ethylene glycol (205.6 g, 3.31M), dry dichloromethane (200 ml), triethylamine (120 ml, 0.86M) and 4-dimethylaminopyridine (8 g, 0.066M) at 0° C. under a nitrogen atmosphere. After the addition the mixture was allowed to warm to ambient temperature and was stirred for a further 3 hours. The mixture was then filtered and the filtrate washed with dilute sodium bicarbonate solution, brine, dried over magnesium sulphate, filtered and then evaporated in vacuo to give a pale yellow oil.

Workup

  1. additionAfter the addition the mixture
  2. filtrationThe mixture was then filtered
  3. washthe filtrate washed with dilute sodium bicarbonate solution, brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a pale yellow oil

Sources & evidence

ORD record
ord-71d56f7843c34c92b8e9452de76d3000
Source dataset
uspto-grants-1995_06
Patent number
US05422402

Reaction notes

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