Sodium Methoxide → 5-Hydroxy-4,4-dimethyl-pentanoic acid methyl ester

HRID 217233Notes

Reaction equation

HRID 217233 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][C:5]1([CH3:12])[CH2:10][O:9][C:8](=[O:11])[CH2:7][CH2:6]1>CO>[CH3:1][O:2][C:8](=[O:11])[CH2:7][CH2:6][C:5]([CH3:12])([CH3:4])[CH2:10][OH:9]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 124481785,5-dimethyltetrahydro-2H-pyran-2-one

Product 1

HCID 576867345-Hydroxy-4,4-dimethyl-pentanoic acid methyl esterYield 933.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of sodium methoxide (6.32 mg, 0.117 mmol) in anhydrous MeOH (346 mL), 5,5-dimethyl-tetrahydro-pyran-2-one (150 mg, 1.17 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). The filtrate is concentrated under reduced pressure to give 5-hydroxy-4,4-dimethyl-pentanoic acid methyl ester (175 mg, 93%); TLC (hexane/AcOEt, 2:1) Rf 0.27, 1H NMR (400 MHz, chloroform-d) δ ppm 0.89 (s, 6H), 1.63 (m, 2H), 2.32 (m, 2H), 3.28 (d, 2H), 3.68 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-85a286b4035d42ee8ceebfc85bed7d34
Source dataset
uspto-grants-2012_06
Patent number
US08193349B2

Reaction notes

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