Methyl acetoacetate → Methyl 2-[3-(methoxymethyl)benzyl]-3-oxobutanoate

HRID 45227Notes

Reaction equation

HRID 45227 reaction equation
[Na].[C:2]([O:8][CH3:9])(=[O:7])[CH2:3][C:4]([CH3:6])=[O:5].Br[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][CH3:20])[CH:13]=1>CO>[CH3:20][O:19][CH2:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:11][CH:3]([C:4](=[O:5])[CH3:6])[C:2]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 5360545SodiumHCID 57975474125604-03-7

Product 1

HCID 86659737Methyl 2-[3-(methoxymethyl)benzyl]-3-oxobutanoateYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 0.34 g (15.1 mmol) of sodium in 8 mL of anhydrous MeOH are added dropwise, at room temperature and under argon, 1.6 mL (15.1 mmol) of methyl acetoacetate. After stirring for 30 minutes, 3.25 g (15.11 mmol) of 1-(bromomethyl)-3-(methoxymethyl)benzene are rapidly added dropwise and the reaction medium is then heated for 2 hours 30 minutes at 70° C. The reaction medium is then concentrated under reduced pressure, and the residue obtained is purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc. 3.2 g of methyl 2-[3-(methoxymethyl)benzyl]-3-oxobutanoate are obtained in the form of an oil.

Workup

  1. concentrationThe reaction medium is then concentrated under reduced pressure
  2. customthe residue obtained
  3. customis purified by chromatography on a column of silica gel
  4. washeluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc

Sources & evidence

ORD record
ord-8f3535271f394776b2680fde3015ddd2
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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