Hydrochloric Acid → HCID 59714895, compound

HRID 2223927Notes

Reaction equation

HRID 2223927 reaction equation
C1(=[CH:9][C:10]([O:12][CH2:13]C)=[O:11])CCCCCCC1.[H-].C([Al+][CH2:21][CH:22]([CH3:24])[CH3:23])C(C)C.[CH3:25][CH2:26][CH2:27][CH2:28][CH2:29]C.Cl>O1CCCC1>[C:10]([O:12][CH2:13][CH:24]=[C:22]1[CH2:21][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:23]1)(=[O:11])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14002565Ethyl cyclooctylideneacetateHCID 21273587HCID 21273587, compound

Product 1

HCID 59714895HCID 59714895, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of ethyl cyclooctylideneacetate (4.82 g) in tetrahydrofuran (25 mL) was added 1M diisobutylaluminum hydride/hexane (73.8 mL) dropwise over 15 minutes. After stirring the reaction solution under ice cooling for 30 minutes, 2N hydrochloric acid (50 mL) was added. After allowing the solution for its temperature rise to room temperature, it was stirred for additional 30 minutes. The reaction solution was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and dried over under reduced pressure. To the resulting residue were added pyridine (22 mL), acetic anhydride (10.1 mL) and N,N-dimethylaminopyridine (0.26 g) sucessively. The solution was stirred at room temperature for 18 hours. The reaction solution was diluted with ethyl acetate, washed in turn with 2N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (97:3)] to give the title compound (3.41 g).

Workup

  1. customto room temperature
  2. stirringit was stirred for additional 30 minutes
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customdried over under reduced pressure
  6. additionTo the resulting residue were added pyridine (22 mL), acetic anhydride (10.1 mL) and N,N-dimethylaminopyridine (0.26 g) sucessively
  7. stirringThe solution was stirred at room temperature for 18 hours
  8. additionThe reaction solution was diluted with ethyl acetate
  9. washwashed in turn with 2N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (97:3)]

Sources & evidence

ORD record
ord-bd38f5b47c60424492a732b692d90ad8
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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