Sodium hydride → S-Triphenylmethyl 2-Methoxyethanethiol

HRID 842423Notes

Reaction equation

HRID 842423 reaction equation
[H-].[Na+].[C:3]1([C:9]([SH:22])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S(C1C=CC(C)=CC=1)(O[CH2:27][CH2:28][O:29][CH3:30])(=O)=O>C1COCC1>[C:3]1([C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[S:22][CH2:27][CH2:28][O:29][CH3:30])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 86977Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)

Product 1

HCID 22614061S-Triphenylmethyl 2-MethoxyethanethiolYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To sodium hydride (2.17 g, 0.09 mol) under nitrogen was added anhydrous THF (50 ml). The mixture was cooled to 0° C. and triphenylmethylmercaptan (24.88 g, 0.09 mol) in anhydrous THF (50 ml) added dropwise over 15 minutes. After a further 10 minutes at 0° C. the mixture was warmed to room temperature, at which it was stirred for 1 hour. The mixture was then recooled to 0° C. and ethylene glycol methyl ether tosylate (20.72 g, 0.09 mol) in dry THF (50 ml) added dropwise over 15 minutes. After warming to room temperature the mixture was left to stir for 16 hours. The mixture was filtered and the precipitate washed with dichloromethane. The combined filtrates were concentrated in vacuo. The residue was dissolved in dichloromethane, washed with water (3×50 ml), dried (Na2SO4) and concentrated in vacuo. Purification by flash column chromatography (gradient from 100% petrol to 100% EtOAc) and recrystallisation (petrol) gave the title compound (12.39 g, 41%) as a pale brown solid.

Workup

  1. temperatureAfter a further 10 minutes at 0° C. the mixture was warmed to room temperature, at which it
  2. customwas then recooled to 0° C.
  3. temperatureAfter warming to room temperature the mixture
  4. waitwas left
  5. stirringto stir for 16 hours
  6. filtrationThe mixture was filtered
  7. washthe precipitate washed with dichloromethane
  8. concentrationThe combined filtrates were concentrated in vacuo
  9. dissolutionThe residue was dissolved in dichloromethane
  10. washwashed with water (3×50 ml)
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated in vacuo
  13. customPurification
  14. customby flash column chromatography (gradient from 100% petrol to 100% EtOAc) and recrystallisation (petrol)

Sources & evidence

ORD record
ord-af18155ee5bc4cf2b8caec6abfaf7bf4
Source dataset
uspto-grants-2002_04
Patent number
US06375926B1

Reaction notes

Loading…