Diethyl Ether → 2-(1H-indol-3-yl)ethane-1-thiol

HRID 502504Notes

Reaction equation

HRID 502504 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][S:12]S(=O)(=O)O)=[CH:2]1.CCOCC>P(=O)(O)(O)O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][SH:12])=[CH:2]1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 12255474Thiosulfuric acid S-[2-(1H-indol-3-yl)-ethyl]ester

Product 1

HCID 122442792-(1H-indol-3-yl)ethane-1-thiol

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

Thiosulfuric acid S-[2-(1H-indol-3-yl)-ethyl]ester, O-sodium salt (5.04 g, 18 mmol) was suspended in 105 ml of 50% phosphoric acid and covered with a layer of 160 ml of ether. The mixture was refluxed for 6 hours. After cooling, the phases were separated and the aqueous phase was extracted with ether and the organic phases were concentrated to dryness by evaporation. The crude product was obtained in a yield of 3.2 g (100%).

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. temperatureAfter cooling
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with ether
  5. concentrationthe organic phases were concentrated to dryness by evaporation

Sources & evidence

ORD record
ord-9cdd961442fd4204a99de19222bc8455
Source dataset
uspto-grants-2010_08
Patent number
US07776848B2

Reaction notes

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