HCID 57615144, compound → HCID 57615147, compound

HRID 1640327Notes

Reaction equation

HRID 1640327 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6][CH2:7][C:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>ClC1C=CC=CC=1>[CH2:9]([C:8]1[C:3]2[CH:4]=[CH:5][S:1][C:2]=2[S:6][CH:7]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 1

HCID 57615144HCID 57615144, compound

Product 1

HCID 57615147HCID 57615147, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 1-(thiophen-2-ylsulfanyl)-dodecan-2-one (3.40 g, 11.4 mmol) and amberlyst 15 (5.5 g) in chlorobenzene (200 mL) are refluxed over 4 A molecular sieves (Soxhlet) for 16 h. The reaction is cooled, filtered and concentrated under reduced pressure. The resulting residue is dissolved in petrol and filtered though a small plug of silica to remove coloured impurities. The organics are concentrated under reduced pressure and further purified by column chromatography over RP18 silica (eluant:acetonitrile). The first fraction is collected to afford the product as a colourless oil (1.8 g, 56%). M/Z 280 (M+). 1H NMR (300 MHz, CDCl3) δ 7.34 (1H, dd), 7.18 (1H, d), 6.93 (1H, d), 2.75 (2H, t), 1.70 (2H, quint), 1.40-1.20 (14H, m), 0.88 (3H, t). 13C NMR (75 MHz, CDCl3) δ 147.3, 136.9, 135.1, 127.8, 122.4, 119.0, 31.9, 29.8, 29.65, 29.63, 29.50, 29.49 (2C), 29.4, 22.7, 14.2.

Workup

  1. temperatureThe reaction is cooled
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting residue is dissolved in petrol
  5. filtrationfiltered though a small plug of silica
  6. customto remove coloured impurities
  7. concentrationThe organics are concentrated under reduced pressure
  8. customfurther purified by column chromatography over RP18 silica (eluant:acetonitrile)
  9. customThe first fraction is collected

Sources & evidence

ORD record
ord-e70f3a4f928946d68564061ff6acccf4
Source dataset
uspto-grants-2012_02
Patent number
US08114316B2

Reaction notes

Loading…