Ethylene Glycol → HCID 21696089, compound

HRID 508397Notes

Reaction equation

HRID 508397 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].N1C=CC=CC=1.[CH2:14]([OH:17])[CH2:15][OH:16]>C(Cl)Cl>[C:2](=[O:3])([O:4][CH:5]([CH3:7])[CH3:6])[O:16][CH2:15][CH2:14][OH:17]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 1049PyridineHCID 7917Isopropyl chloroformate

Product 1

HCID 21696089HCID 21696089, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of isopropyl chloroformate (2 g, 0.016 mol.) in 10 mL of DCM at 0° C. under nitrogen atmosphere was added pyridine (3.8 mL, 0.048 mol) and then ethylene glycol (2.7 mL, 3 eq). The progress of the reaction was monitored by thin layer chromatography (TLC). After stirring for 15 hrs at room temperature. After removing the solvent under reduce pressure, the residue was purified by silica gel column chromatography to give 2-hydroxyethyl isopropyl carbonate as a colorless oil (0.5 g, 42% yield). 1HNMR (400 MHz, CDCl3): δ 1.22 (t, J=7.2 Hz, 3H); 2.94 (sbroad, 1H); 3.78 (t, J=4.4 Hz, 2H); 4.18 (t, J=4.4 Hz, 2H); 4.07 (q, J=7.2H, 2H).

Workup

  1. customAfter removing the solvent
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4f5ec28ff6214cacaf42830371ca07c3
Source dataset
uspto-grants-2015_08
Patent number
US09096515B2

Reaction notes

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