4-Toluenesulfonyl chloride → HCID 67247928, compound

HRID 2425324Notes

Reaction equation

HRID 2425324 reaction equation
[CH2:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][C:13](=[O:18])[CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH:19](OCC)=O.[H-].[Na+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C1COCC1.O>[CH2:1]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[CH2:19])[C:13](=[O:18])[CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 67246552HCID 67246552, compound

Product 1

HCID 67247928HCID 67247928, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Octyl-2-indanone, 2A (5.00 g, 20.5 mmol) and ethyl formate (3.70 g, 50 mmol) are dissolved in toluene (40 mL). Sodium hydride (1.15 g, 50 mmol) is added and the reaction brought to reflux for 6 hours with continuous removal of water. The reaction mixture is cooled to room temperature and p-toluenesulfonyl chloride (3.75 g, 21.0 mmol) dissolved in THF (20 mL) added. The reaction mixture is maintained under inert atmosphere for 12 hours and filtered. The solvent is removed in vacuo to yield a viscous liquid residue. The crude reaction mixture is used without purification in the next step.

Workup

  1. additionadded
  2. temperatureThe reaction mixture is maintained under inert atmosphere for 12 hours
  3. filtrationfiltered
  4. customThe solvent is removed in vacuo
  5. customto yield a viscous liquid residue
  6. customThe crude reaction mixture
  7. customis used without purification in the next step

Sources & evidence

ORD record
ord-c4fefdef195d47329cdba8008ac0c269
Source dataset
uspto-grants-2011_06
Patent number
US07964649B2

Reaction notes

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