Ethyl vinyl ether → HCID 67500911, compound

HRID 921524Notes

Reaction equation

HRID 921524 reaction equation
[CH:1]([O:3][CH2:4][CH3:5])=[CH2:2].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[Cl:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[NH:28][N:29]=[C:30]([CH2:31][CH3:32])[C:23]=12.C(=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[Cl:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[N:28]([CH:1]([O:3][CH2:4][CH3:5])[CH3:2])[N:29]=[C:30]([CH2:31][CH3:32])[C:23]=12

Participants

7

Reactant 4

HCID 8023Ethyl vinyl etherHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 516892Sodium BicarbonateHCID 178438029HCID 178438029, compound

Product 1

HCID 67500911HCID 67500911, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl vinyl ether (3.7 mL) and (+)-10-camphorsulfonic acid (0.162 g) were sequentially added to a solution of compound (3c) (2.36 g) in THF (13.0 mL), followed by stirring at 50° C. for 30 min. After cooling, the reaction solution was distributed between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and then the solvent was distilled away. The residue was purified by neutral silica gel column chromatography (n-hexane/ethyl acetate) to obtain compound (3d) (3.01 g, 91%) as an oily substance.

Workup

  1. temperatureAfter cooling
  2. washThe organic layer was washed with saturated saline
  3. dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away
  5. customThe residue was purified by neutral silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-987602baf54746da95dcc680c209485e
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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