Methyl acetoacetate → 2-(2-Benzyloxy-ethyl)-3-oxo-butyric acid methyl ester

HRID 916654Notes

Reaction equation

HRID 916654 reaction equation
[H-].[Na+].[C:3]([O:9][CH3:10])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.Br[CH2:28][CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>COCCOC>[CH3:10][O:9][C:3](=[O:8])[CH:4]([CH2:28][CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:5](=[O:6])[CH3:7]

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 1859152-Naphthylalanine

Product 1

HCID 119536662-(2-Benzyloxy-ethyl)-3-oxo-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a suspension of NaH (2.0 g, 60% in mineral oil) in DME (50 ml) at 0° C. is added dropwise a solution of methyl acetoacetate (5.8 g, 50 mmol) in DME (10 mL). The solution is stirred at room temperature for 30 minutes. Nal (7.5 g) is added in one portion and then benzyl bromoethyl ether (10.7 5 g, 50 mmol). The mixture is stirred at 70–80° C. overnight. After the formed solid is removed, the solvent is removed. The residue is purified by column with 4:1 of hexane to ethyl acetate to a colorless oil (159).

Workup

  1. stirringThe mixture is stirred at 70–80° C. overnight
  2. customAfter the formed solid is removed
  3. customthe solvent is removed
  4. customThe residue is purified by column with 4:1 of hexane to ethyl acetate to a colorless oil (159)

Sources & evidence

ORD record
ord-8def3045dfaf4f9ba37950c68e1b1731
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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