Diethyl Carbonate → HCID 20063132, compound

HRID 931093Notes

Reaction equation

HRID 931093 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([C:14]([CH2:19][OH:20])([CH2:17]O)[CH2:15][OH:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)(OCC)OCC>O1CCCC1>[CH2:7]([C:14]1([CH2:15][OH:16])[CH2:17][O:20][CH2:19]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 23665647Potassium tert-butoxideHCID 58388140HCID 58388140, compound

Product 1

HCID 20063132HCID 20063132, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
110 °C

Procedure

A solution of potassium t-butoxide in tetrahydrofuran (1M, 24 mL) was added into a solution of 2-benzyl-2-(hydroxymethyl)propane-1,3-diol (90 g, 0.5 mol) and diethyl carbonate (55 g, 0.5 mol) in tetrahydrofuran (500 mL) under nitrogen. The reaction mixture was refluxed for 6 h and then heated to 110° C. to distill the solvent. Then the mixture was stirred at 155° C. for 24 h. The mixture was purified via silica gel chromatography (petroleum ether/ethyl acetate 10:1 to 2:1) to afford (3-benzyloxetan-3-yl)methanol (40 g, 0.226 mol, 49%) was a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. distillationto distill the solvent
  3. customThe mixture was purified via silica gel chromatography (petroleum ether/ethyl acetate 10:1 to 2:1)

Sources & evidence

ORD record
ord-e9d7624677cd49519d96a9ae1540e140
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

Loading…