Thiophenol → HCID 11805926, compound

HRID 2260421Notes

Reaction equation

HRID 2260421 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-]CC.[Na+].[CH:12]12[O:18][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]2>C(O)C>[C:1]1([S:7][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[OH:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 9246Cyclohexene oxideHCID 2723922Sodium ethoxide

Product 1

HCID 11805926HCID 11805926, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiophenol (2.14 g, 0.0194 mole) was added to freshly prepared sodium ethoxide (sodium, 0.45 g) in ethanol (30 ml). After several minutes, cyclohexene oxide was added, and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated with a gentle flow of nitrogen gas. The residue was dissolved in diethyl ether (75 ml) and washed with in hydrochloric acid (19 ml). The diethyl ether was washed three times with 50 ml of 5% sodium carbonate, once with 0.5N hydrochloric acid (50 ml) and once with brine (25 ml), dried over anhydrous magnesium sulphate, filtered and concentrated with a rotary evaporator to give the product as an oil. The structure was supported by NMR and infrared spectroscopy.

Workup

  1. waitAfter several minutes
  2. concentrationThe reaction mixture was concentrated with a gentle flow of nitrogen gas
  3. dissolutionThe residue was dissolved in diethyl ether (75 ml)
  4. washwashed with in hydrochloric acid (19 ml)
  5. washThe diethyl ether was washed three times with 50 ml of 5% sodium carbonate
  6. dry with materialonce with 0.5N hydrochloric acid (50 ml) and once with brine (25 ml), dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated with a rotary evaporator

Sources & evidence

ORD record
ord-3a2e4afca75d41ecabf57dc8eaa14183
Source dataset
uspto-grants-1995_12
Patent number
US05476944

Reaction notes

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