Dibenzyl ethylmalonate → 2-Formyl-butyric acid, benzyl ester

HRID 1245563

Reaction equation

HRID 1245563 reaction equation
[CH2:1]([CH:3]([C:14](OCC1C=CC=CC=1)=[O:15])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])[CH3:2]>CCCCCC.CCOC(C)=O>[CH:14]([CH:3]([CH2:1][CH3:2])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])=[O:15]

Participants

3

Reactant 1

HCID 53752489Dibenzyl ethylmalonate

Product 1

HCID 867602822-Formyl-butyric acid, benzyl ester

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared from ethylmalonic acid, dibenzyl ester (from Step A) using a procedure analogous to that described for Aldehyde 3, Step B. RF: 0.35 (9:1 v/v hexane/EtOAc); 1H-NMR (500 MHz: Equilibrium mixture of aldehyde and enol) δ 0.92–1.00 (m), 1.04–1.08 (m), 1.93–2.01 (m), 2.14–2.18 (m), 5.17, 5.23, 5.26 (3s), 7.05 (d, J=12.6), 7.30–7.41 (m), 9.74 (d, J=2.3), 11.33 (d, J=12.6).

Sources & evidence

ORD record
ord-04c5368c49dd4b719bbdaaa9ad4a0143
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Linked notes

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