2-[2-[2-(2-sulfanylethoxy)ethoxy]ethoxy]ethanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-{2-[2-(2-mercapto-ethoxy)-ethoxy]-ethoxy}-ethanol (310 mg, 1.47 mmol) and trityl chloride (452 mg, 1.62 mmol, 1.1 eq.) in a round bottomed flask was added simultaneously triethylamine (2.1 ml, 10 eq.) and THF (25 ml) under argon. The initial red colour faded upon stirring at ambient temperature for 1 hour. The reaction was monitored by TLC, ethyl acetate/ethanol (1:1) and was completed after 6 hours. Thereafter methanol (6 ml) was added to consume excess trityl chloride and the mixture stirred for 5 minutes before evaporation of the solvents. The residue was purified by flash chromatography using 100% ethyl acetate to afford the product (550 mg, 83%) as a colourless oil. was completed after 6 hours to consume excess trityl chloride the mixture stirred for 5 minutes before evaporation of the solvents The residue was purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-{2-[2-(2-mercapto-ethoxy)-ethoxy]-ethoxy}-ethanol (310 mg, 1.47 mmol) and trityl chloride (452 mg, 1.62 mmol, 1.1 eq.) in a round bottomed flask was added simultaneously triethylamine (2.1 ml, 10 eq.) and THF (25 ml) under argon. The initial red colour faded upon stirring at ambient temperature for 1 hour. The reaction was monitored by TLC, ethyl acetate/ethanol (1:1) and was completed after 6 hours. Thereafter methanol (6 ml) was added to consume excess trityl chloride and the mixture stirred for 5 minutes before evaporation of the solvents. The residue was purified by flash chromatography using 100% ethyl acetate to afford the product (550 mg, 83%) as a colourless oil. was completed after 6 hours to consume excess trityl chloride the mixture stirred for 5 minutes before evaporation of the solvents The residue was purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of thiourea (0.94 g, 12.35 mmol) and toluene-4-sulfonic acid 2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy)-ethyl ester (4.09 g, 11.75 mmol) in absolute alcohol (32 ml) was heated to reflux under argon atmosphere for 24 h. The mixture was cooled and a solution of NaOH (1.23 g, 30.75 mmol) in 15 ml of ethanol/water (9:1, v/v) was added. Refluxing was continued for another 2.5 h under argon. The reaction mixture was then cooled to ambient temperature and acidified to pH 2 using concentrated hydrochloric acid and then concentrated under reduced pressure. The residue was purified by flash chromatography using ethyl acetate/absolute ethanol (10:1) to afford the product as a colourless oil. Yield 1.55 g (66%). to reflux under argon atmosphere for 24 h The mixture was cooled Refluxing concentrated under reduced pressure The residue was purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of thiourea (0.94 g, 12.35 mmol) and toluene-4-sulfonic acid 2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy)-ethyl ester (4.09 g, 11.75 mmol) in absolute alcohol (32 ml) was heated to reflux under argon atmosphere for 24 h. The mixture was cooled and a solution of NaOH (1.23 g, 30.75 mmol) in 15 ml of ethanol/water (9:1, v/v) was added. Refluxing was continued for another 2.5 h under argon. The reaction mixture was then cooled to ambient temperature and acidified to pH 2 using concentrated hydrochloric acid and then concentrated under reduced pressure. The residue was purified by flash chromatography using ethyl acetate/absolute ethanol (10:1) to afford the product as a colourless oil. Yield 1.55 g (66%). to reflux under argon atmosphere for 24 h The mixture was cooled Refluxing concentrated under reduced pressure The residue was purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of thiourea (0.94 g, 12.35 mmol) and toluene-4-sulfonic acid 2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy)-ethyl ester (4.09 g, 11.75 mmol) in absolute alcohol (32 ml) was heated to reflux under argon atmosphere for 24 h. The mixture was cooled and a solution of NaOH (1.23 g, 30.75 mmol) in 15 ml of ethanol/water (9:1, v/v) was added. Refluxing was continued for another 2.5 h under argon. The reaction mixture was then cooled to ambient temperature and acidified to pH 2 using concentrated hydrochloric acid and then concentrated under reduced pressure. The residue was purified by flash chromatography using ethyl acetate/absolute ethanol (10:1) to afford the product as a colourless oil. Yield 1.55 g (66%). to reflux under argon atmosphere for 24 h The mixture was cooled Refluxing concentrated under reduced pressure The residue was purified by flash chromatography