Ammonia → Sulfonium, triphenyl-, 7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-methanesulfonate (1:1)

HRID 1168015

Reaction equation

HRID 1168015 reaction equation
[I-].[C:2]1([S+:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])(OCC)C.[C:28]12([CH2:38][S:39]([OH:42])(=[O:41])=[O:40])[C:35]([CH3:37])([CH3:36])[CH:32]([CH2:33][CH2:34]1)[CH2:31][C:29]2=[O:30].N>C(Cl)Cl>[C:28]12([CH2:38][S:39]([O-:42])(=[O:40])=[O:41])[C:35]([CH3:37])([CH3:36])[CH:32]([CH2:33][CH2:34]1)[CH2:31][C:29]2=[O:30].[C:15]1([S+:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 21881071Triphenylsulfonium iodideHCID 86598186Ethyl ortho-acetate

Product 1

HCID 21930749Sulfonium, triphenyl-, 7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-methanesulfonate (1:1)Yield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylsulfonium iodide (390 mg; 1 mmol), ethyl orthoacetate (486 mg; 3 mmol), and camphorsulfonic acid (278 mg; 1.2 mmol) were dissolved in anhydrous methylene chloride (10 ml), and the resultant mixture was stirred for 12 hours at room temperature. The reaction mixture was alkalinized by adding 1% aqueous ammonia (10 ml), and subjected to extraction with methylene chloride three times, followed by drying. The solvent was removed through distillation, and the thus-obtained semi-solid matter was washed with ether, to thereby yield 410 mg of the target compound as white crystals (yield: 82%).

Workup

  1. extractionsubjected to extraction with methylene chloride three times
  2. customby drying
  3. customThe solvent was removed through distillation
  4. washthe thus-obtained semi-solid matter was washed with ether

Sources & evidence

ORD record
ord-d973bf890c0347a4b9a1e922835f7e82
Source dataset
uspto-grants-2003_09
Patent number
US06620957B1

Linked notes

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