Water → HCID 10760318, compound

HRID 1492469Notes

Reaction equation

HRID 1492469 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][CH2:11][C@@H:12]1[C@@H:17]([CH2:18][OH:19])[CH2:16][CH:15]=[CH:14][CH2:13]1.CN([CH2:23][CH2:24][CH2:25]N)C.[OH2:27]>N1C=CC=CC=1>[C:1]([O:10][CH2:11][C@@H:12]1[C@@H:17]([CH2:18][O:19][C:23](=[O:27])[C:24]2[CH:25]=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH2:16][CH:15]=[CH:14][CH2:13]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 10942538HCID 10942538, compound

Product 1

HCID 10760318HCID 10760318, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Benzoyl chloride (2.0 ml, 17 mmoles) was slowly added to a solution of (4S,5S)-4,5-bis(hydroxymethyl)-1-cyclohexene (1.00 g, 7.0 mmoles) in pyridine (7 ml) while cooling the system with ice. The resulting mixture was stirred at 0° C. for one hour. After adding dimethylaminopropylamine (0.8 ml, 6.4 mmoles) to the reaction mixture and stirring it at that temperature for 15 minutes, water was added and the product formed was extracted with ethyl ether. The ether extract solution was washed successively with water, dilute hydrochloric acid and saturated aqueous solution of sodium chloride and then dried on anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9, v/v) to obtain (4S,5S)-4,5-bis(benzoyloxymethyl)- 1-cyclohexene (2.5 g, Yield 100%).

Workup

  1. temperaturewhile cooling the system with ice
  2. stirringstirring it at that temperature for 15 minutes
  3. customthe product formed
  4. extractionwas extracted with ethyl ether
  5. extractionThe ether extract solution
  6. washwas washed successively with water, dilute hydrochloric acid and saturated aqueous solution of sodium chloride
  7. dry with materialdried on anhydrous sodium sulfate
  8. distillationAfter distilling off the solvent under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9, v/v)

Sources & evidence

ORD record
ord-71e00abd61f74767aa19545b28eac555
Source dataset
uspto-grants-1994_12
Patent number
US05374625

Reaction notes

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