Pyridine → 3-(Toluenesulphonylethoxy)thiophene

HRID 981784Notes

Reaction equation

HRID 981784 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.O[CH2:13][CH2:14][O:15][C:16]1[CH:20]=[CH:19][S:18][CH:17]=1.N1C=CC=C[CH:22]=1>>[C:3]1([CH3:22])[C:4]([S:7]([CH2:13][CH2:14][O:15][C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)(=[O:8])=[O:9])=[CH:5][CH:6]=[CH:1][CH:2]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 220362782-(Thiophen-3-yloxy)-ethanol

Product 1

HCID 679392993-(Toluenesulphonylethoxy)thiophene

Conditions

Temperature
-20 °C

Procedure

Solid p-toluenesulphonyl chloride (0.88 g, 4.6 mmol) was added in small amounts to a cooled (-5° C.) solution of 3-(hydroxyethoxy)thiophene (0.6 g, 4.2 mmol) in dry pyridine (50 ml). The mixture was stirred for 10 minutes and then maintained at -20° C. for 48 hours. The mixture was then stirred with crushed ice for 5 hours. After filtration, the solid was recrystallised twice from hot hexane to give 3-(toluenesulphonylethoxy)thiophene as a white crystalline product, (1.0 g, 83%) M.p. 76°-77° C.; (Found: C, 52.1; H, 4.5; N, 21.8. Calculated for C13H14S2O4C, 52.3; H, 4.7; N, 21.5%); EI m/e Intensity (%): 298 (0.5 M+), 199 (57, Tosyl-OCH2CH2); δH(CDCl3) 7.3-7.7 (4H, m), 7.0 (1H, m), 6.5 (1H, m), 6.0 (1H, m), 4.2 (2H, t), 4.0 (2H, t), 2.4 (3H, s); δC(CDCl3): 21.7, 67.5, 68.0, 98.1, 119.3, 125.0, 128.0, 129.9 ppm.

Workup

  1. stirringThe mixture was then stirred with crushed ice for 5 hours
  2. filtrationAfter filtration
  3. customthe solid was recrystallised twice from hot hexane

Sources & evidence

ORD record
ord-c9d5a01d1a3e46d08ee2b9b54e76aeaf
Source dataset
uspto-grants-1991_02
Patent number
US04992559

Reaction notes

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