Pyridine → Toluene-4-sulfonic acid 2-cyclopropyl-ethyl ester

HRID 1887238Notes

Reaction equation

HRID 1887238 reaction equation
[CH:1]1([CH2:4][CH2:5][OH:6])[CH2:3][CH2:2]1.N1C=CC=CC=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>ClCCl>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:6][CH2:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 1376422-Cyclopropylethan-1-ol

Product 1

HCID 13568392Toluene-4-sulfonic acid 2-cyclopropyl-ethyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-cyclopropylethanol (5.00 g, 58.05 mmol) in dichloromethane (20 mL) was added pyridine (7.03 mL, 86.92 mmol), followed by p-toluenesulfonyl chloride (10.50 g, 55.07 mmol). The reaction mixture was stirred for 16 h, and then partitioned between dichloromethane (100 mL) and water (50 mL). The organic layer was washed with 10% aqueous hydrochloric acid (50 mL), saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford 2-cyclopropylethyl 4-methylbenzenesulfonate as a colorless oil (11.90 g, 96%): 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=8.3 Hz, 2H), 7.34 (d, J=8.3 Hz, 2H), 4.09 (t, J=6.6 Hz, 2H), 2.45 (s, 3H), 1.57-1.48 (m, 2H), 0.74-0.59 (m, 1H), 0.45-0.36 (m, 2H), 0.08-0.06 (m, 2H).

Workup

  1. custompartitioned between dichloromethane (100 mL) and water (50 mL)
  2. washThe organic layer was washed with 10% aqueous hydrochloric acid (50 mL), saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-81fd0621b75d467389faacde4290b4fa
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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