Potassium Carbonate → HCID 23070270, compound

HRID 351299Notes

Reaction equation

HRID 351299 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[SH:6].[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH2:10]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH2:10][S:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 5226742-Thiophenethiol

Product 1

HCID 23070270HCID 23070270, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-thiophenethiol (12.3 g, 106 mmol) in acetone (180 ml), bromoacetaldehyde dimethyl acetal (13.6 ml, 115 mmol) was added, followed by potassium carbonate (21.8 g, 158 mmol). The reaction was refluxed for 16 h, cooled, then filtered and concentrated under reduced pressure. The crude product was purified by column chromatography over silica (eluent: petrol:DCM, 2:1) to afford the product as an orange oil (21.0 g, 97%). M/Z 204 (M+). Found C, 47.0; H, 5.7; S, 32.3; O, 15.8. Calc. for C8H12O2S2 C, 47.0; H 5.9; S, 31.4; O, 15.7. 1H NMR (300 MHz, CDCl3) δ 7.35 (dd, 1H, J=1.22 & 5.37 Hz), 7.17 (dd, 1H, J=1.22 & 3.58 Hz), 6.97 (dd, 1H, J=3.58 & 5.37 Hz), 4.51 (t,1 H, J=5.65 Hz), 3.35 (s, 6H), 2.98 (d, 2H, J=5.65 Hz).

Workup

  1. temperatureThe reaction was refluxed for 16 h
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography over silica (eluent: petrol:DCM, 2:1)

Sources & evidence

ORD record
ord-9f8b9f6e031a4a7e99bafd4ae20db869
Source dataset
uspto-grants-2007_02
Patent number
US07183418B2

Reaction notes

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