Potassium Carbonate → HCID 57615144, compound

HRID 1640326Notes

Reaction equation

HRID 1640326 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[SH:6].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:14][C:15](=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CC(C)=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6][CH2:14][C:15](=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5226742-ThiophenethiolHCID 15257396HCID 15257396, compound

Product 1

HCID 57615144HCID 57615144, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of thiophene-2-thiol (2.0 g, 17.2 mmol) in dry acetone (100 ml) is added anhydrous potassium carbonate (2.8 g; 20 mmol), followed by 1-chlorododecan-2-one (3.8 g, 17.2 mmol) dropwise. The reaction is stirred for 30 min and RT, filtered and concentrated under reduced pressure. The crude product is further purified by column chromatography (eluent: petrol/ethyl acetate 100:0 to 95:5) to afford the product as a colourless oil (3.66 g, 71%). M/Z 298 (M+). 1H NMR (300 MHz, CDCl3) δ 7.36 (1H, dd), 7.15 (1H, dd), 6.96 (1H, dd), 3.55 (2H, s), 2.55 (2H, t), 1.57 (2H, m), 1.35-1.20 (14H, m), 0.88 (3H, t). 13C NMR (75 MHz, CDCl3) δ 205.1, 134.6, 132.5, 130.3, 127.7, 48.2, 41.1, 31.9, 29.6, 29.5, 29.4, 29.3, 29.1, 23.8, 22.7, 14.1.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product is further purified by column chromatography (eluent: petrol/ethyl acetate 100:0 to 95:5)

Sources & evidence

ORD record
ord-3c523dd983fd4744ae912b36e8726a1c
Source dataset
uspto-grants-2012_02
Patent number
US08114316B2

Reaction notes

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