Delta-Valerolactone → Pentanoic acid, 5-hydroxy-, methyl ester

HRID 217227

Reaction equation

HRID 217227 reaction equation
[CH3:1][O-:2].[Na+].[O:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[O:10]>CO>[CH3:1][O:2][C:9](=[O:4])[CH2:8][CH2:7][CH2:6][CH2:5][OH:10]

Participants

4

Reactant 2

HCID 10953Delta-ValerolactoneHCID 10942334Sodium Methoxide

Product 1

HCID 3014818Pentanoic acid, 5-hydroxy-, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of sodium methoxide (71.3 mg, 1.32 mmol) in anhydrous MeOH (4 ml), tetrahydro-pyran-2-one (1.32 g, 13.2 mmol) is added dropwise at room temperature under nitrogen. The mixture is stirred at 50° C. for 4 hours and filtered through a silica gel short column (eluent: diethyl ether). Collected filtrate is concentrated under reduced pressure to give 5-hydroxy-pentanoic acid methyl ester; 1H NMR (400 MHz, chloroform-d) ppm 1.57-1.76 (m, 4H), 2.35 (m, 2H), 3.65 (m, 5H).

Workup

  1. filtrationfiltered through a silica gel short column (eluent: diethyl ether)
  2. concentrationCollected filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-4f67e378ad1149a29304e130c34d5861
Source dataset
uspto-grants-2012_06
Patent number
US08193349B2

Linked notes

Loading…