Dimethylolpropionic acid → Propanoic acid, 3-hydroxy-2-(hydroxymethyl)-2-methyl-, methyl ester

HRID 631488Notes

Reaction equation

HRID 631488 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH3:7])[C:4]([OH:6])=[O:5].[CH3:10][Si](C=[N+]=[N-])(C)C>CO.C(OCC)C>[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH3:7])[C:4]([O:6][CH3:10])=[O:5]

Participants

5

Reactant 2

HCID 78501Dimethylolpropionic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 87346Propanoic acid, 3-hydroxy-2-(hydroxymethyl)-2-methyl-, methyl esterYield 34%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoic acid (10.06 g, 75 mmol) in MeOH was dropped 2.0 M solution of (trimethylsilyl)diazomethane in diethyl ether and stirred at room temperature overnight. After solvent was concentrated under reduced pressure, the reaction was quenched with saturated NaHCO3 solution and extracted with CH2Cl2. Extracts were dried over MgSO4 and concentrated under reduced pressure to afford methyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate as an oil (3.79 g, 34%). 1H NMR (300 MHz, CDCl3) δ 3.81 (d, 2H), 3.67 (s, 3H), 3.60 (d, 2H), 2.89 (br, 2H), 0.96 (s, 3H).

Workup

  1. concentrationAfter solvent was concentrated under reduced pressure
  2. customthe reaction was quenched with saturated NaHCO3 solution
  3. extractionextracted with CH2Cl2
  4. dry with materialExtracts were dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-62bc599981f844acbd88692f8342c16c
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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