Triethylamine → HCID 86631897, compound

HRID 1161617Notes

Reaction equation

HRID 1161617 reaction equation
[C:1]([O:5][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([OH:16])([CH2:9]3)[CH2:7]1)[CH2:13]2)(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].S([O-])([O-])(=O)=O.[Mg+2]>O.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]12[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][C:8]([O:16][S:25]([CH3:24])(=[O:27])=[O:26])([CH2:9]3)[CH2:7]1)[CH2:13]2)(=[O:4])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 31297Methanesulfonyl chloride2×HCID 222287903-Hydroxy-1-adamantyl acrylate

Product 1

HCID 86631897HCID 86631897, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A stirrer and a dropping funnel were equipped with a 3 L-glass reactor. Then, 222.3 g (1.0 mol) of Adamantate HA (manufactured by Idemitsu Kosan Co., Ltd.: 3-hydroxy-1-adamantyl acrylate), 151.8 g (1.5 mol) of dried triethylamine, and 2,000 mL of dried toluene were added into the glass reactor, and were stirred at 0° C. in an ice bath. Subsequently, 137.5 g (1.2 mol) of methanesulfonyl chloride was added thereto, and was stirred for 5 minutes. As a result of conducting gas chromatography-mass spectrography analysis, it was confirmed that the peak of the adamantate HA was completely disappeared. Subsequently, 100 mL of water was added into it, thereby unreacted methanesulfonyl chloride was deactivated. The reaction solution thus obtained was transferred to a 4 L-separating funnel, 800 mL of water was further added, and then the reaction solution was sufficiently stirred. After leaving at rest, the aqueous layer was removed. To remove the triethylamine, 500 mL of 0.5 N hydrochloric acid was added, and stirred. After leaving at rest, the aqueous layer was removed. Furthermore, an organic layer was washed using an aqueous saturated sodium hydrogen carbonate and an aqueous saturated sodium chloride. This organic layer was transferred to a conical flask, and 12.0 g (0.1 mol) of anhydrous magnesium sulfate was added. The magnesium sulfate was removed by filtration after being dried. Then, the toluene was distilled away from the filtrate by evaporation. As a result of conducting GC analysis, it was confirmed that compound 1 (chemical formula shown below) having purity of 95.4% was obtained (yield 301.6 g).

Workup

  1. customA stirrer and a dropping funnel were equipped with a 3 L-glass reactor
  2. stirringwas stirred for 5 minutes
  3. customAs a result
  4. customThe reaction solution thus obtained
  5. customseparating funnel
  6. addition800 mL of water was further added
  7. stirringthe reaction solution was sufficiently stirred
  8. customAfter leaving at rest
  9. customthe aqueous layer was removed
  10. customTo remove the triethylamine, 500 mL of 0.5 N hydrochloric acid
  11. additionwas added
  12. stirringstirred
  13. customAfter leaving at rest
  14. customthe aqueous layer was removed
  15. washFurthermore, an organic layer was washed
  16. customThis organic layer was transferred to a conical flask
  17. customThe magnesium sulfate was removed by filtration
  18. customafter being dried
  19. distillationThen, the toluene was distilled away from the filtrate by evaporation
  20. customAs a result
  21. customwas obtained (yield 301.6 g)

Sources & evidence

ORD record
ord-a8a285293c85403f9866c643c6b0ebda
Source dataset
uspto-grants-2010_10
Patent number
US07820360B2

Reaction notes

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