Water → HCID 21954436, compound

HRID 2414993Notes

Reaction equation

HRID 2414993 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-4977a530341844a1a1a4e5bf8e40b5cb
Source dataset
uspto-grants-2004_11
Patent number
US06818377B2

Reaction notes

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