4-Toluenesulfonyl chloride → HCID 86627792, compound

HRID 645478Notes

Reaction equation

HRID 645478 reaction equation
[CH3:1][C:2]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C.Cl.CN(C)C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:1][C:2]1([CH2:6][O:7][S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 52090138401-41-1HCID 10313079Trimethylamine Hydrochloride

Product 1

HCID 86627792HCID 86627792, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1-methylcyclobutyl)methanol (32 mmol) in CH2Cl2 (100 mL) are added triethylamine (65 mmol), trimethylamine hydrochloride (6 mmol), and a solution of p-toluenesulfonyl chloride (49 mmol) in CH2Cl2 (50 mL) at 0° C., then the mixture is stirred at 0° C. for 0.5 h. The reaction is quenched by the addition of water, and the mixture is extracted with CH2Cl2. The combined organic extracts are washed with water and brine. The organic layer is dried over Na2SO4, filtered, and concentrated in vacuo to give toluene-4-sulfonic acid 1-methylcyclobutylmethyl ester, which is directly used for the next reaction without further purification.

Workup

  1. customThe reaction is quenched by the addition of water
  2. extractionthe mixture is extracted with CH2Cl2
  3. washThe combined organic extracts are washed with water and brine
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78c550eec3484d33a1c62317bda987c6
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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