Diethyl butylmalonate → HCID 54237698, compound

HRID 1590931Notes

Reaction equation

HRID 1590931 reaction equation
[CH2:1]([CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:2][CH2:3][CH3:4].OC1[CH2:22][C:21]([CH3:24])([CH3:23])[N:20]([O:25][CH3:26])[C:19]([CH3:28])([CH3:27])C1>[NH2-].[Li+].C1(C)C(C)=CC=CC=1>[CH2:1]([CH:5]([C:11]([O:13][CH:14]1[CH2:24][C:21]([CH3:22])([CH3:23])[N:20]([O:25][CH3:26])[C:19]([CH3:27])([CH3:28])[CH2:15]1)=[O:12])[C:6]([O:8][CH:9]1[CH2:22][C:21]([CH3:24])([CH3:23])[N:20]([O:25][CH3:26])[C:19]([CH3:28])([CH3:27])[CH2:10]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 67244Diethyl butylmalonateHCID 109977701-Methoxy-2,2,6,6-tetramethyl-piperidin-4-ol

Product 1

HCID 54237698HCID 54237698, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 24532Lithium amideCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of diethyl n-butylmalonate (11.55 g, 53.4 mmol), 4-hydroxy-1-methoxy-2,2,6,6-tetramethylpiperidine (20.0 g, 107 mmol), lithium amide (120 mg), and xylene (100 ml) is distilled until the distillate reaches a constant temperature of 137° C. Xylene is evaporated and the residue is dissolved in heptane. Acetic acid is added and the resulting precipitate is filtered. The filtrate is concentrated to obtain 26.2 g (98% yield) of a light yellow oil.

Workup

  1. distillationis distilled until the distillate
  2. customa constant temperature of 137° C
  3. customXylene is evaporated
  4. dissolutionthe residue is dissolved in heptane
  5. additionAcetic acid is added
  6. filtrationthe resulting precipitate is filtered
  7. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-20b921b2568c4c88ab22a6e9bf4f0c09
Source dataset
uspto-grants-1993_04
Patent number
US05204473

Reaction notes

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