Ethyl phenylacetate → HCID 57062398, compound

HRID 2083026Notes

Reaction equation

HRID 2083026 reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-]CC.[Na+].[Na].[CH2:18]=[C:19]1[C:24](=[O:25])[CH:23]2[CH2:26][CH2:27][N:20]1[CH2:21][CH2:22]2>C(O)C.C(O)(=O)C>[O:25]=[C:24]1[CH:23]2[CH2:26][CH2:27][N:20]([CH2:21][CH2:22]2)[CH:19]1[CH2:18][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 4

HCID 7590Ethyl phenylacetateHCID 3229732-Methylene-3-quinuclidoneHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 57062398HCID 57062398, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Procedure

Ethyl phenylacetate, 49.2 g was added to a solution of sodium ethoxide previously prepared from metallic sodium, 2.9 g and ethanol, 100 ml. The mixture was cooled to 5°, then a solution of 2-methylenequinuclidin-3-one, 39.4 g, in ethanol, 50 ml. was added dropwise and with stirring. After 16 hours at room temperature, the solution was neutralized with acetic acid then subjected to evaporation at reduced pressure. Water, 100 ml. was added to the residue and the mixture was extracted with chloroform. Evaporation of this solvent gave ethyl (3-oxoquinuclidin-2-yl)methylphenylacetate, 54 g (60%); b.p. 195°-200° at 1 mm Hg; m.p. of methiodide salt, 194.7°-195.6°.

Workup

  1. temperatureThe mixture was cooled to 5°
  2. additionwas added dropwise
  3. customthen subjected to evaporation at reduced pressure
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. customEvaporation of this solvent

Sources & evidence

ORD record
ord-0bf5bb9172ed482a8f7bf261ff5f733c
Source dataset
uspto-grants-1978_04
Patent number
US04083985

Reaction notes

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