4-Methylbenzenethiol → 2-p-Tolylsulfanylcarbonyl-cyclopropanecarboxylic acid ethyl ester

HRID 1836650Notes

Reaction equation

HRID 1836650 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9](Cl)=[O:10])=[O:5])[CH3:2].[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.CCN(CC)CC>CCCCCC>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]([S:19][C:16]1[CH:17]=[CH:18][C:13]([CH3:12])=[CH:14][CH:15]=1)=[O:10])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 78114-MethylbenzenethiolHCID 8471TriethylamineHCID 12547528HCID 12547528, compound

Product 1

HCID 865876872-p-Tolylsulfanylcarbonyl-cyclopropanecarboxylic acid ethyl esterYield 99.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

To a solution of 2-chlorocarbonyl-cyclopropanecarboxylic acid ethyl ester (5.30 g, 30 mmol) and 4-methylbenzene thiol (3.73 g, 30 mmol) in 150 mL hexane at 0° C. was added a solution of Et3N in 25 mL hexane dropwise. The reaction was warmed to room temperature and stirred for 3 h. The solid precipitate was removed by filtration and washed with hexane. The filtrate was concentrated in vacuo to give 7.88 g (99%) of 2-p-tolylsulfanylcarbonyl-cyclopropanecarboxylic acid ethyl ester as an oil: 1H NMR (500 MHz, CDCl3) 7.30 (2H, d, J=7.93 Hz), 7.22 (2H, d, J=7.93 Hz), 4.17 (2H, q, J=7.02 Hz), 2.60 (1H, m), 2.37 (3H, s), 2.31 (H, m), 1.54 (2H, m), 1.29 (3H, t, J=7.02 Hz). MS m/e 262.92 (M−H)−. Anal. calcd. for C14H16O3S: C, 63.61; H, 6.10. Found: C, 63.68; H, 6.17.

Workup

  1. customThe solid precipitate was removed by filtration
  2. washwashed with hexane
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f91ae98c58104c618bc05fb632dc49d6
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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