Sodium hydride → HCID 58358729, compound

HRID 922818Notes

Reaction equation

HRID 922818 reaction equation
C(O[C:4](=[O:18])[CH2:5][C@H:6]1[CH2:11][CH2:10][CH2:9][C@@H:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7]1)C.[H-].[Na+]>COCCOC>[CH2:16]([O:15][C:13]([CH:12]1[C:4](=[O:18])[CH2:5][CH:6]2[CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11]2)=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 58358703HCID 58358703, compound

Product 1

HCID 58358729HCID 58358729, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
94 °C

Procedure

Cis-cyclohexane-1,3-diacetic acid diethyl ester QU was dissolved in dry DME (300 mL). To this solution, sodium hydride (15 g) was added and the suspension stirred at 94° C. for 16 h. After cooling, the reaction mixture was slowly poured into ice-water (500 mL) and extracted four times with EtOAc (200 mL each). The combined organic layer was washed with brine, and concentrated to give 3-oxo-bicyclo[3.3.1]nonane-2-carboxylic acid ethyl ester QV which was used without purification in the next step.

Workup

  1. temperatureAfter cooling
  2. extractionextracted four times with EtOAc (200 mL each)
  3. washThe combined organic layer was washed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e522700e070b46e99543516db9e1de34
Source dataset
uspto-grants-2016_03
Patent number
US09278967B2

Reaction notes

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