Pyridine → HCID 53762272, compound

HRID 54153Notes

Reaction equation

HRID 54153 reaction equation
[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:4]=1[CH2:5][C:6]1([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.CCN(CC)CC.N1C=CC=CC=1.CCOC(C)=O>CS(C)=O>[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:4]=1[CH2:5][C:6]1([CH:13]=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 19961173[1-(2,3-Dimethoxybenzyl)cycloheptyl]methanol

Product 1

HCID 53762272HCID 53762272, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

The alcohol from Step C above (25 g, 89 mmol) was dissolved in 500 mL of anhydrous DMSO. To this solution was added Et3N (50 mL, 358 mmol). Then SO3.Pyridine (57 g, 358 mmol), was dissolved in 400 mL of DMSO, and this solution was added to the reaction vessel. The solution was then stirred at room temperature for two hours. The reaction solution was then poured over ice and the resulting mixture was warmed to room temperature and extracted with CH2Cl2. The organic layer was washed with 1M HCl, water, and brine, then the organic layer was dried over MgSO4, filtered and evaporated. The crude product was chromatographed on silica gel, eluting with 10:1 hexane:EtOAc to give the title product as a colorless oil (20 g, 81% yield).

Workup

  1. additionthis solution was added to the reaction vessel
  2. additionThe reaction solution was then poured over ice
  3. temperaturethe resulting mixture was warmed to room temperature
  4. extractionextracted with CH2Cl2
  5. washThe organic layer was washed with 1M HCl, water, and brine
  6. dry with materialthe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was chromatographed on silica gel
  10. washeluting with 10:1 hexane

Sources & evidence

ORD record
ord-34ae82ec46294e1f90e675899fae7f5e
Source dataset
uspto-grants-1997_04
Patent number
US05621133

Reaction notes

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