Triethylamine → HCID 67189857, compound

HRID 546354Notes

Reaction equation

HRID 546354 reaction equation
[C:1]1([CH:7]2[O:12][CH2:11][CH:10]([OH:13])[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:21]12([C:31](Cl)=[O:32])[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2>CN(C)C1C=CN=CC=1.ClCCl>[C:21]12([C:31]([O:13][CH:10]3[CH2:11][O:12][CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[O:8][CH2:9]3)=[O:32])[CH2:28][CH:27]3[CH2:26][CH:25]([CH2:24][CH:23]([CH2:29]3)[CH2:22]1)[CH2:30]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 743621,3-Dioxan-5-ol, 2-phenyl-HCID 989151-Adamantanecarbonyl chloride

Product 1

HCID 67189857HCID 67189857, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1.00 g (5.55 mmol) of 2-phenyl[1.3]dioxan-5-ol, 1.16 ml (8.32 mmol) of triethylamine and 68 mg (0.56 mmol) of 4-dimethylaminopyridine were dissolved in 20 ml of dichloromethane, and 1.28 g (6.10 mmol) of 1-adamantanecarbonyl chloride was added thereto with stirring under ice-cooling, followed by stirring for 30 minutes at the same temperature, and then further for 15 hours at room temperature. Dichloromethane was distilled off under reduced pressure, and to the residue was added aqueous sodium hydrogencarbonate and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; hexane:ethyl acetate=9:1) to give 1.52 g of the title compound as a pale yellow powder (yield: 80%).

Workup

  1. temperaturecooling
  2. stirringby stirring for 30 minutes at the same temperature
  3. distillationDichloromethane was distilled off under reduced pressure
  4. additionto the residue was added aqueous sodium hydrogencarbonate
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-fde5613f244f466d99cab381c95ba61a
Source dataset
uspto-grants-2011_05
Patent number
US07935835B2

Reaction notes

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