Cyclooctanol → HCID 57567227, compound

HRID 1727336Notes

Reaction equation

HRID 1727336 reaction equation
[CH:1]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10]([O:15][CH2:16][CH2:17][N:18]=[C:19]=[O:20])(=[O:14])[C:11]([CH3:13])=[CH2:12]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C(Cl)Cl>[CH:1]1([O:9][C:19]([NH:18][CH2:17][CH2:16][O:15][C:10](=[O:14])[C:11]([CH3:13])=[CH2:12])=[O:20])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 12766CyclooctanolHCID 354092-Isocyanatoethyl methacrylate

Product 1

HCID 57567227HCID 57567227, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of cyclooctanol (3.00 grams, 23 millimoles), 2-isocyanatoethyl methacrylate (3.63 grams, 23 millimoles), methylene chloride (10 milliliters), and one drop of dibutyltin dilaurate were stirred at 50° C. for three hours. The solvent was then removed under reduced pressure and the crude product was purified by column chromatography over silica gel using a mixture of ethyl acetate/hexane (20/80). The product was isolated as an oil (5.20 grams, 80% yield). Purity and structure verification of Comparative Example C5 were confirmed by 1H NMR.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe crude product was purified by column chromatography over silica gel using
  3. additiona mixture of ethyl acetate/hexane (20/80)

Sources & evidence

ORD record
ord-85a36af5840c472dab0e8000ae5633f0
Source dataset
uspto-grants-2009_02
Patent number
US07495054B2

Reaction notes

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