Tetrahydrofuran → (2-Ethyl-1,3-dioxolan-2-yl)methanol

HRID 1645601Notes

Reaction equation

HRID 1645601 reaction equation
[CH2:1]([C:3]1([CH2:8][C:9](OC)=O)[O:7][CH2:6][CH2:5][O:4]1)C.C(=O)([O-])[O-:14].[K+].[K+].O1CCCC1>O>[CH2:8]([C:3]1([CH2:1][OH:14])[O:4][CH2:5][CH2:6][O:7]1)[CH3:9]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 13085711Methyl (2-ethyl-1,3-dioxolan-2-yl)acetate

Product 1

HCID 59792561(2-Ethyl-1,3-dioxolan-2-yl)methanolYield 71.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl (2-ethyl-1,3-dioxolan-2-yl)acetate (1.39 g, 7.94 mmol), potassium carbonate (2.19 g, 15.9 mmol), tetrahydrofuran (20 ml) and water (10 ml) was stirred at room temperature for 6 hours and 50 minutes. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, which was subjected to NH silica gel pad filtration. The filtrate was concentrated under reduced pressure to obtain the title compound (0.75 g, 71.5%) as colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. additionwas added to the residue, which
  3. filtrationwas subjected to NH silica gel pad filtration
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3ee2feaf5bb04bcdb6bce30c28a8ecbc
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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