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

HRID 871531Notes

Reaction equation

HRID 871531 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-75efd7b933c94d3eafd203cd1537e80c
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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