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

HRID 56869Notes

Reaction equation

HRID 56869 reaction equation
Cl[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:19]([OH:22])[CH2:20][OH:21].N1C=CN=C1>O1CCCC1>[Si:2]([O:21][CH2:20][CH2:19][OH:22])([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 795ImidazoleHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 151562692-((tert-Butyldiphenylsilyl)oxy)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.0 g (36.4 mmol) of chloro-tert-butyl(diphenyl)silane dissolved in 88 ml of tetrahydrofuran were added dropwise over a period of 6 h to a solution of 10.1 ml (182 mmol) of 1,2-ethanediol and 2.97 g (43.7 mmol) of imidazole in 12 ml of tetrahydrofuran, and the mixture was then stirred further at RT overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (340 g silica cartridge, 100 ml/min, cyclohexane/ethyl acetate gradient). Yield: 8.34 g (76% of theory)

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (340 g silica cartridge, 100 ml/min, cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-2d86c1d81b9e4ec2be5562bd6e27da76
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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