2-[1-(2-hydroxyethyl)cyclopropyl]ethanol

Conditions: temp:-50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.0 ml (79.9 mmol) of oxalyl chloride were dissolved in 45 ml of abs. dichloromethane, the mixture was cooled to −50° C. and a solution of 10.9 ml (163.6 mmol) of DMSO in 45 ml of abs. dichloromethane was added dropwise. After the end of the addition, the mixture was stirred at −50° C. for another 10 min, and 4.0 g (30.7 mmol) of 2,2′-cyclopropane-1,1-diyldiethanol, dissolved in 45 ml of abs. dichloromethane, were then added slowly. The resulting suspension was stirred at −50° C. for 10 min and then cooled to −78° C., and a solution of 44.5 ml (320 mmol) of triethylamine in 75 ml of abs. dichloromethane was added dropwise. After the end of the addition, the reaction mixture was stirred at −78° C. for 30 min and then slowly warmed to RT and subsequently washed with saturated aqueous sodium bisulphate solution. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. This gave 5.10 g of the target product as an orange oil (crude product of a purity of about 70%, about 92% of theory). After the end of the addition The resulting suspension was stirred at −50° C. for 10 min cooled to −78° C. After the end of the addition the reaction mixture was stirred at −78° C. for 30 min slowly warmed to RT subsequently washed with saturated aqueous sodium bisulphate solution The organic phase was dried over sodium sulphate concentrated under reduced pressure

Conditions: temp:-50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.0 ml (79.9 mmol) of oxalyl chloride were dissolved in 45 ml of abs. dichloromethane, the mixture was cooled to −50° C. and a solution of 10.9 ml (163.6 mmol) of DMSO in 45 ml of abs. dichloromethane was added dropwise. After the end of the addition, the mixture was stirred at −50° C. for another 10 min, and 4.0 g (30.7 mmol) of 2,2′-cyclopropane-1,1-diyldiethanol, dissolved in 45 ml of abs. dichloromethane, were then added slowly. The resulting suspension was stirred at −50° C. for 10 min and then cooled to −78° C., and a solution of 44.5 ml (320 mmol) of triethylamine in 75 ml of abs. dichloromethane was added dropwise. After the end of the addition, the reaction mixture was stirred at −78° C. for 30 min and then slowly warmed to RT and subsequently washed with saturated aqueous sodium bisulphate solution. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. This gave 5.10 g of the target product as an orange oil (crude product of a purity of about 70%, about 92% of theory). After the end of the addition The resulting suspension was stirred at −50° C. for 10 min cooled to −78° C. After the end of the addition the reaction mixture was stirred at −78° C. for 30 min slowly warmed to RT subsequently washed with saturated aqueous sodium bisulphate solution The organic phase was dried over sodium sulphate concentrated under reduced pressure

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

Procedure: 109.5 g (crude product, about 547 mmol) of ethyl methyl 2,2′-cyclopropane-1,1-diyldiacetate were dissolved in 750 ml of p.a. THF, and, at −20° C., 984 ml (984 mmol) of a 1 M solution of lithium aluminium hydride in THF were added dropwise. The reaction mixture was warmed to RT overnight and, after cooling again to −10° C., 500 ml of isopropanol were added carefully. The mixture was acidified with 1 N hydrochloric acid and filtered off with suction through Celite. The residue was washed with ethyl acetate and water. The filtrate was saturated with sodium chloride and extracted repeatedly with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The residue was recrystallized from acetonitrile. This gave 50.4 g of the target product (70.8% of theory). after cooling again to −10° C. filtered off with suction through Celite The residue was washed with ethyl acetate and water extracted repeatedly with ethyl acetate The combined organic phases were dried over sodium sulphate concentrated under reduced pressure The residue was recrystallized from acetonitrile

Conditions: temp:-50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.0 ml (79.9 mmol) of oxalyl chloride were dissolved in 45 ml of abs. dichloromethane, the mixture was cooled to −50° C. and a solution of 10.9 ml (163.6 mmol) of DMSO in 45 ml of abs. dichloromethane was added dropwise. After the end of the addition, the mixture was stirred at −50° C. for another 10 min, and 4.0 g (30.7 mmol) of 2,2′-cyclopropane-1,1-diyldiethanol, dissolved in 45 ml of abs. dichloromethane, were then added slowly. The resulting suspension was stirred at −50° C. for 10 min and then cooled to −78° C., and a solution of 44.5 ml (320 mmol) of triethylamine in 75 ml of abs. dichloromethane was added dropwise. After the end of the addition, the reaction mixture was stirred at −78° C. for 30 min and then slowly warmed to RT and subsequently washed with saturated aqueous sodium bisulphate solution. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. This gave 5.10 g of the target product as an orange oil (crude product of a purity of about 70%, about 92% of theory). After the end of the addition The resulting suspension was stirred at −50° C. for 10 min cooled to −78° C. After the end of the addition the reaction mixture was stirred at −78° C. for 30 min slowly warmed to RT subsequently washed with saturated aqueous sodium bisulphate solution The organic phase was dried over sodium sulphate concentrated under reduced pressure

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

Procedure: 109.5 g (crude product, about 547 mmol) of ethyl methyl 2,2′-cyclopropane-1,1-diyldiacetate were dissolved in 750 ml of p.a. THF, and, at −20° C., 984 ml (984 mmol) of a 1 M solution of lithium aluminium hydride in THF were added dropwise. The reaction mixture was warmed to RT overnight and, after cooling again to −10° C., 500 ml of isopropanol were added carefully. The mixture was acidified with 1 N hydrochloric acid and filtered off with suction through Celite. The residue was washed with ethyl acetate and water. The filtrate was saturated with sodium chloride and extracted repeatedly with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The residue was recrystallized from acetonitrile. This gave 50.4 g of the target product (70.8% of theory). after cooling again to −10° C. filtered off with suction through Celite The residue was washed with ethyl acetate and water extracted repeatedly with ethyl acetate The combined organic phases were dried over sodium sulphate concentrated under reduced pressure The residue was recrystallized from acetonitrile