Sodium hydride → HCID 58358729, compound

HRID 84158Notes

Reaction equation

HRID 84158 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-b6237bf04a024de3a98cb0661f75ea46
Source dataset
uspto-grants-2014_09
Patent number
US08846929B2

Reaction notes

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