Potassium Hydroxide → HCID 85967320, compound

HRID 902923Notes

Reaction equation

HRID 902923 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([C:14]([O:16]CC)=[O:15])[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH3:2].[OH-].[K+]>C(O)C>[C:10]([O:9][C:7](=[O:8])[CH2:6][CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:19])[C:14]([OH:16])=[O:15])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11346360diethyl [(1,1-dimethylethoxycarbonyl)methyl]-malonate

Product 1

HCID 85967320HCID 85967320, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the tri-ester of example 21 (38 g, 0.14 mol) in ethanol (456 mL) was added 77.6 mL of a 10% aqueous solution of potassium hydroxide. The resulting mixture was refluxed for 3 hours. The isolated product was purified by flash chromatography (SiO2, 90% dichloromethane-10% methanol) to afford 20.68 g (60.6% yield) of the title compound: 1H NMR (CDCl3, 400 MHz) 4.16 (q, 2H), 3.72 (t, 1H), 2.80 (d, 2H), 1.35 (s, 9H), 1.20 (t, 3H); 13C NMR (CDCl3, 400 MHz) 170.0, 168.9, 81.6, 62.4, 47.7, 34.5, 28.2, 14.5.

Workup

  1. temperatureThe resulting mixture was refluxed for 3 hours
  2. customThe isolated product was purified by flash chromatography (SiO2, 90% dichloromethane-10% methanol)

Sources & evidence

ORD record
ord-f39cea9d95d6459cb15f97f5416b45cd
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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