3-Chloropropanal

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

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: A vigorously stirred solution of 3-propionyl-2-benzoxazolone (19.1 g) in 200 mL of CH2Cl2 at 0° C. was treated with titanium tetrachloride (12.0 mL) followed by slow addition of triethylamine (16.7 mL). After stirring for 30 minutes, the dark red solution was treated with 60 mL of 1.8 M 3-chloropropanal in CH2Cl2 for 30 minutes, then quenched by addition of 200 mL of 2 N HCl. The phases were separated, and the organic phase was filtered through a pad of silica gel. The aqueous phase was extracted with ether, and the extract was used to wash the pad of silica. The combined silica eluate was concentrated under reduced pressure, resulting in crystallization. The white crystals were collected by vacuum filtration and dried to provide 19.9 g of product; mp=116-117° C. quenched by addition of 200 mL of 2 N HCl The phases were separated the organic phase was filtered through a pad of silica gel The aqueous phase was extracted with ether to wash the pad of silica The combined silica eluate was concentrated under reduced pressure resulting in crystallization The white crystals were collected by vacuum filtration dried

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

Procedure: To 68 ml. of 1.6M butyllithium in hexane at -50° C. is added dropwise, with stirring, 7.4 g. of 1-pentyne. The resulting white sludge is diluted with 20 ml. of hexane, brought to 10° C. and treated with 11 g. of freshly prepared β-chloropropionaldehyde (Org. Syn., Coll. Vol. I, p. 166) at such a rate that the temperature is maintained at 10°-15° C. The solution is allowed to stir at ambient temperature for 18 hours then treated with saturated ammonium chloride solution. The organic phase is separated, washed with dilute hydrochloric solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation gives 5.1 g. of product b.p. 65°-66° C. at 0.3 nm.; λ max. 2.95 (--OH) and 4.55μ (-C≡C-); vapor phase chromatography shows one peak. The resulting white sludge is diluted with 20 ml brought to 10° C. treated with 11 g to stir at ambient temperature for 18 hours The organic phase is separated washed with dilute hydrochloric solution dried with anhydrous magnesium sulfate Distillation gives 5.1 g

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

Procedure: To 68 ml. of 1.6M butyllithium in hexane at -50° C. is added dropwise, with stirring, 7.4 g. of 1-pentyne. The resulting white sludge is diluted with 20 ml. of hexane, brought to 10° C. and treated with 11 g. of freshly prepared β-chloropropionaldehyde (Org. Syn., Coll. Vol. I, p. 166) at such a rate that the temperature is maintained at 10°-15° C. The solution is allowed to stir at ambient temperature for 18 hours then treated with saturated ammonium chloride solution. The organic phase is separated, washed with dilute hydrochloric solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation gives 5.1 g. of product b.p. 65°-66° C. at 0.3 nm.; λ max. 2.95 (--OH) and 4.55μ (-C≡C-); vapor phase chromatography shows one peak. The resulting white sludge is diluted with 20 ml brought to 10° C. treated with 11 g to stir at ambient temperature for 18 hours The organic phase is separated washed with dilute hydrochloric solution dried with anhydrous magnesium sulfate Distillation gives 5.1 g

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

Procedure: To 68 ml. of 1.6 M butyllithium in hexane at -50° C. is added dropwise, with stirring, 7.4 g. of 1-pentyne. The resulting white sludge is diluted with 20 ml. of hexane, brought to 10° C. and treated with 11 g. of freshly prepared β-chloropropionaldehyde (Org. Syn., Coll. Vol. I, p. 166) at such a rate that the temperature is maintained at 10°-15° C. The solution is allowed to stir at ambient temperature for 18 hours then treated with saturated ammonium chloride solution. The organic phase is separated, washed with dilute hydrochloric solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation gives 5.1 g. of product b.p. 65°-66° C. at 0.3 nm.; λmax. 2.95 (--OH) and 4.55μ (--C≡C--); vapor phase chromatography shows one peak. The resulting white sludge is diluted with 20 ml brought to 10° C. treated with 11 g to stir at ambient temperature for 18 hours The organic phase is separated washed with dilute hydrochloric solution dried with anhydrous magnesium sulfate Distillation gives 5.1 g

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

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

Procedure: To 68 ml. of 1.6 M butyllithium in hexane at -50° C. is added dropwise, with stirring, 7.4 g. of 1-pentyne. The resulting white sludge is diluted with 20 ml. of hexane, brought to 10° C. and treated with 11 g. of freshly prepared β-chloropropionaldehyde (Org. Syn., Coll. Vol. I, p. 166) at such a rate that the temperature is maintained at 10°-15° C. The solution is allowed to stir at ambient temperature for 18 hours then treated with saturated ammonium chloride solution. The organic phase is separated, washed with dilute hydrochloric solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation gives 5.1 g. of product b.p. 65°-66° C. at 0.3 nm.; λmax. 2.95 (--OH) and 4.55μ (--C≡C--); vapor phase chromatography shows one peak. The resulting white sludge is diluted with 20 ml brought to 10° C. treated with 11 g to stir at ambient temperature for 18 hours The organic phase is separated washed with dilute hydrochloric solution dried with anhydrous magnesium sulfate Distillation gives 5.1 g

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

Procedure: To 68 ml. of 1.6M butyllithium in hexane at -50° C. is added dropwise, with stirring, 7.4 g. of 1-pentyne. The resulting white sludge is diluted with 20 ml. of hexane, brought to 10° C. and treated with 11 g. of freshly prepared β-chloropropionaldehyde (Org. Syn., Coll. Vol. I, p. 166) at such a rate that the temperature is maintained at 10°-15° C. The solution is allowed to stir at ambient temperature for 18 hours then treated with saturated ammonium chloride solution. The organic phase is separated, washed with dilute hydrochloric solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation gives 5.1 g. of product b.p. 65°-66° C. at 0.3 nm.; λmax. 2.95 (--OH) and 4.55 μ (--C≡C--); vapor phase chromatography shows one peak. The resulting white sludge is diluted with 20 ml brought to 10° C. treated with 11 g to stir at ambient temperature for 18 hours The organic phase is separated washed with dilute hydrochloric solution dried with anhydrous magnesium sulfate Distillation gives 5.1 g

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

Procedure: To 68 ml. of 1.6 M butyllithium in hexane at -50° C. is added dropwise, with stirring, 7.4 g. of 1-pentyne. The resulting white sludge is diluted with 20 ml. of hexane, brought to 10° C. and treated with 11 g. of freshly prepared β-chloropropionaldehyde (Org. Syn., Coll. Vol. I, p. 166) at such a rate that the temperature is maintained at 10°-15° C. The solution is allowed to stir at ambient temperature for 18 hours then treated with saturated ammonium chloride solution. The organic phase is separated, washed with dilute hydrochloric solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation gives 5.1 g. of product b.p. 65°-66° C. at 0.3 nm.; λmax. 2.95 (--OH) and 4.55μ (--C≡C--); vapor phase chromatography shows one peak. The resulting white sludge is diluted with 20 ml brought to 10° C. treated with 11 g to stir at ambient temperature for 18 hours The organic phase is separated washed with dilute hydrochloric solution dried with anhydrous magnesium sulfate Distillation gives 5.1 g

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

Procedure: To 68 ml. of 1.6M butyllithium in hexane at -50°C. is added dropwise, with stirring, 7.4 g. of 1-pentyne. The resulting white sludge is diluted with 20 ml. of hexane, brought to 10°C. and treated with 11 g. of freshly prepared β-chloropropionaldehyde (Org. Syn., Coll. Vol. I, p. 166) at such a rate that the temperature is maintained at 10°-Coll. C. The solution is allowed to stir at ambient temperature for 18 hours then treated with saturated ammonium chloride solution. The organic phase is separated, washed with dilute hydrochloric solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation gives 5.1 g. of product b.p. 65°-66°C. at 0.3 nm.; λmax. 2.95 (-OH) and 4.55 μ (--C≡C--); vapor phase chromatography shows one peak. The resulting white sludge is diluted with 20 ml brought to 10°C. treated with 11 g to stir at ambient temperature for 18 hours The organic phase is separated washed with dilute hydrochloric solution dried with anhydrous magnesium sulfate Distillation gives 5.1 g