Pyridine → HCID 20441011, compound

HRID 1633402Notes

Reaction equation

HRID 1633402 reaction equation
[C:1]([C:4]1([CH2:13][OH:14])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)([CH3:3])=[CH2:2].N1C=CC=CC=1.[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>CCOCC>[S:21]([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)([O:14][CH2:13][C:4]1([C:1]([CH3:3])=[CH2:2])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 20441017HCID 20441017, compound

Product 1

HCID 20441011HCID 20441011, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 3.20 g (0.017 mole) of 2-isopropenyl-2-indanemethanol and 3.16 g (0.04 mole) of pyridine, with ice-cooling, was added 3.90 g (0.02 mole) of tosylchloride. The mixture was stirred for 24 hours, with ice-cooling, to complete the reaction. The reaction mixture was poured into ice water, mixed with 50 ml of ether. And then the ether layer was separated, the aqueous layer was extracted twice with 25 ml of ether. The ether layers were combined, washed with 2% aqueous hydrochloric acid solution, then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain 5.80 g of 2-iso-propenyl-2-indanylmethyl tosylate.

Workup

  1. temperaturewith ice-cooling
  2. temperaturecooling
  3. customthe reaction
  4. customAnd then the ether layer was separated
  5. extractionthe aqueous layer was extracted twice with 25 ml of ether
  6. washwashed with 2% aqueous hydrochloric acid solution
  7. dry with materialwith saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8f85f1c99ba4f12b14308698198f48d
Source dataset
uspto-grants-1984_10
Patent number
US04480118

Reaction notes

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