HCID 22718200, compound → HCID 22718206, compound

HRID 1582761Notes

Reaction equation

HRID 1582761 reaction equation
[C:1]([C:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH:11]([CH3:13])[CH3:12])[CH2:4][CH2:5][CH:6]([OH:10])[CH2:7][CH2:8][CH3:9])#[N:2]>CS(C)=O.C(N(CC)CC)C>[C:1]([C:3]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([CH:11]([CH3:13])[CH3:12])[CH2:4][CH2:5][C:6](=[O:10])[CH2:7][CH2:8][CH3:9])#[N:2]

Participants

4

Reactant 1

HCID 22718200HCID 22718200, compound

Product 1

HCID 22718206HCID 22718206, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8471TriethylamineSolvent

Procedure

7-Cyano-8-methyl-7-phenylnonane-4-ol, 70 mg 0.27 mmol, was dissolved in dimethyl sulfoxide 3.00 ml and triethylamine 0.70 ml. A sulfur trioxide-pyridine complex 64.7 mg was added thereto. After 1 hour, an additional sulfur trioxide-pyridine complex 80.0 mg was added thereto. The reaction mixture was partitioned by adding aqueous saturated sodium bicarbonate and ethyl acetate. The organic layer was washed with aqueous ammonium chloride and then with brine, dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 50 mg 0.19 mmol, 72.0%, was obtained as a colorless syrup.

Workup

  1. additionA sulfur trioxide-pyridine complex 64.7 mg was added
  2. additionan additional sulfur trioxide-pyridine complex 80.0 mg was added
  3. customThe reaction mixture was partitioned
  4. additionby adding aqueous saturated sodium bicarbonate and ethyl acetate
  5. washThe organic layer was washed with aqueous ammonium chloride
  6. dry with materialwith brine, dried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 50 mg 0.19 mmol, 72.0%
  9. customwas obtained as a colorless syrup

Sources & evidence

ORD record
ord-942b83c73da54e62ae403be84579f5e5
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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