Water → HCID 21954436, compound

HRID 1596139Notes

Reaction equation

HRID 1596139 reaction equation
C[C:2]1([OH:12])[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[CH2:13](N(CC)CC)C.[C:20](Cl)(=[O:24])[C:21]([CH3:23])=[CH2:22].O>O1CCCC1>[C:20]([O:12][CH:2]1[CH:3]2[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8][C:9]1([CH3:13])[CH2:10]3)[CH2:11]2)(=[O:24])[C:21]([CH3:23])=[CH2:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 1365452-Methyl-2-adamantanol

Product 1

HCID 21954436HCID 21954436, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 300 ml of tetrahydrofuran, 30 g of 2-methyl-2-adamantanol, 36 g of triethylamine and 4 g of N,N-dimethylaminopyridine were dissolved, and to the solution was dropwise added 29 g of methacrylic chloride under cooling with ice over a period of 30 minutes. The temperature of the solution was raised to room temperature and reacted as it was overnight. To the reaction solution was added 500 ml of distilled water under cooling with ice and then extracted with ethyl acetate. The organic layer was dried and concentrated to obtain a crude product. The crude product was purified by column chromatography to obtain 17 g of the desired compound.

Workup

  1. temperatureunder cooling with ice over a period of 30 minutes
  2. customreacted as it
  3. temperatureunder cooling with ice
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customto obtain a crude product
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c0769242b92f45eb82b8b70a29d9458c
Source dataset
uspto-grants-2001_09
Patent number
US06291130B1

Reaction notes

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