Diethyl Malonate → HCID 67585006, compound

HRID 1417754Notes

Reaction equation

HRID 1417754 reaction equation
[H-].[Na+].C1COCC1.C(OCC)(=O)CC(OCC)=O.[C:19]12([C:29]3[CH:49]=[CH:48][C:32]([C:33]([NH:35][C:36]4[CH:47]=[CH:46][C:39]([C:40]([O:42]CC=C)=[O:41])=[CH:38][CH:37]=4)=[O:34])=[CH:31][C:30]=3[O:50][CH2:51][O:52][CH2:53][CH2:54][O:55][CH3:56])[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:19]12([C:29]3[CH:49]=[CH:48][C:32]([C:33]([NH:35][C:36]4[CH:37]=[CH:38][C:39]([C:40]([OH:42])=[O:41])=[CH:46][CH:47]=4)=[O:34])=[CH:31][C:30]=3[O:50][CH2:51][O:52][CH2:53][CH2:54][O:55][CH3:56])[CH2:28][CH:23]3[CH2:22][CH:21]([CH2:27][CH:25]([CH2:24]3)[CH2:26]1)[CH2:20]2

Participants

7

Reactant 4

HCID 7761Diethyl MalonateHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 67572951HCID 67572951, compound

Product 1

HCID 67585006HCID 67585006, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

107 mg (3.5 mmol) of sodium hydride (80% in oil) and 5 ml of THF were introduced into a round-bottomed flask under a stream of nitrogen. 535 μl (3.5 mmol) of diethyl malonate were then added dropwise and the mixture was stirred until the evolution of gas had ceased. This solution was introduced dropwise into a mixture of 1.67 g (3.2 mmol) of allyl 4-[4-(1-adamantyl)-3-methoxyethoxymethoxybenzamido]benzoate, 40 ml of THF and 184 mg (0.18 mmol) of tetrakis(triphenylphosphine)palladium(0) and the mixture was stirred at room temperature for three hours. The reaction medium was poured into water and extracted with ethyl ether. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica, eluted with a mixture of dichloromethane and ethyl acetate (80/20). After evaporation of the solvents, 630 mg (41%) of 4-[4-(1-adamantyl)-3-methoxyethoxymethoxybenzamido]benzoic acid, having a melting point of 189°-91° C., were recovered.

Workup

  1. stirringthe mixture was stirred at room temperature for three hours
  2. extractionextracted with ethyl ether
  3. customThe organic phase was separated out
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customwas purified by chromatography on a column of silica
  8. washeluted with a mixture of dichloromethane and ethyl acetate (80/20)
  9. customAfter evaporation of the solvents, 630 mg (41%) of 4-[4-(1-adamantyl)-3-methoxyethoxymethoxybenzamido]benzoic acid
  10. customwere recovered

Sources & evidence

ORD record
ord-4ff0b236a2d74e87b4e945b306d3c182
Source dataset
uspto-grants-1999_03
Patent number
US05877342

Reaction notes

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