HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 916654
Notes
Print preview

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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8071
1,2-Dimethoxyethane
Solvent
2×

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07271170B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes