Methanol → Methyl 2-(tetrahydrofuran-3-yl)acetate

HRID 541245Notes

Reaction equation

HRID 541245 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2]1.S(=O)(=O)(O)O.[CH3:15]O>CCOCC>[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][C:7]([O:9][CH3:15])=[O:8])[CH2:2]1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 42449052-(Oxolan-3-yl)acetic acid

Product 1

HCID 58216760Methyl 2-(tetrahydrofuran-3-yl)acetateYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-(tetrahydrofuran-3-yl)acetic acid (2.00 g, 15.4 mmol, 1.00 equiv) and sulfuric acid (2 mL) in methanol (20 mL) was stiffed for 3 h at 80° C. in an oil bath. After cooling to ambient temperature, the mixture was diluted with 50 mL of ether and washed with 2×20 mL of water, 2×20 mL of sodium bicarbonate (aq., sat. Note: gas evolution), and 2×20 mL of brine. The organic phase was then dried over anhydrous sodium sulfate and concentrated in vacuo to yield 1.50 g (68%) of the title compound as a yellow oil.

Workup

  1. washwashed with 2×20 mL of water, 2×20 mL of sodium bicarbonate (aq., sat. Note: gas evolution), and 2×20 mL of brine
  2. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a17d607d5954782a714ebb124c66705
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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