Sodium ethoxide → HCID 178525776, compound

HRID 237330Notes

Reaction equation

HRID 237330 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH2:8][CH2:7]1)=[O:5])C.[O-]CC.[Na+]>C1(C)C=CC=CC=1.O1CCOCC1.[OH-].[Na+]>[O:16]1[CH2:15][CH2:14][CH:13]([O:12][C@H:9]2[CH2:10][CH2:11][C@H:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)[CH2:18][CH2:17]1

Participants

6

Reactant 2

HCID 2723922Sodium ethoxideHCID 178472481HCID 178472481, compound

Product 1

HCID 178525776HCID 178525776, compoundYield 104.5%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of cis/trans-4-(tetrahydro-pyran-4-yloxy)-cyclohexanecarboxylic acid ethyl ester (7:1) (0.385 g, 1.50 mmol) and sodium ethoxide (0.204 g, 3.00 mmol) in dry toluene (1.5 ml) was heated at reflux for 20 h. The reaction mixture was cooled to room temperature, diluted with 1,4-dioxane (7.5 ml) and 2 M aqueous sodium hydroxide solution (7.5 ml). Stirring for 16 h was followed by partitioning between 2 M aqueous sodium hydroxide solution (50 ml) and dichloromethane. The layers were separated. The aqueous layer was extracted with one portion of dichloromethane. The combined organic layers were washed with two 50 ml portions of 2 M aqueous sodium hydroxide solution. The combined aqueous layers were acidified to pH 1 by addition of concentrated hydrochloric acid solution (100 ml). The aqueous layer was extracted with two 150-ml portions of dichloromethane. The combined organic layers from the acidic extraction were dried over anhydrous sodium sulfate and dried in vacuo to give the title compound (0.358 g, 93%) as yellow solid. MS m/e: 229 (M+H+)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. customby partitioning between 2 M aqueous sodium hydroxide solution (50 ml) and dichloromethane
  4. customThe layers were separated
  5. extractionThe aqueous layer was extracted with one portion of dichloromethane
  6. washThe combined organic layers were washed with two 50 ml portions of 2 M aqueous sodium hydroxide solution
  7. additionThe combined aqueous layers were acidified to pH 1 by addition of concentrated hydrochloric acid solution (100 ml)
  8. extractionThe aqueous layer was extracted with two 150-ml portions of dichloromethane
  9. extractionThe combined organic layers from the acidic extraction
  10. dry with materialwere dried over anhydrous sodium sulfate
  11. customdried in vacuo

Sources & evidence

ORD record
ord-e68e4edf8f6341ec8f5ba385c4673209
Source dataset
uspto-grants-2014_02
Patent number
US08642590B2

Reaction notes

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